Abstract
Owing to the prevalence of nitrogen-containing compounds in natural products and important pharmaceutical agents, chemists, have actively searched for the development of efficient and selective methodologies allowing for the facile construction of carbon–nitrogen bonds. Over the last decade, transition metal-catalyzed C–N bond construction via electrophilic amination reaction has emerged as an attractive approach for the synthesis of various organic molecules and pharmaceuticals. Particularly, O-benzoylhydroxylamines as an electrophilic aminating agent have proven to be the best and most widely used in both academic and industrial research. In this review, we highlight the key contributions to the recent transition metal-catalyzed C–N bond formation reactions using O-benzoylhydroxylamines as an aminating agent and their relevant mechanistic insights.
Graphical Abstract
Similar content being viewed by others
Data availability
This work is review article, and as such, readers will need to contact referenced authors to obtain additional information regarding the data presented.
References
Zhao Y, **a W (2018) Recent advances in radical-based C–N bond formation: via photo-/electrochemistry. Chem Soc Rev 20:20
Wang Q, Su Y, Li L, Huang H (2016) Transition-metal catalysed C–N bond activation. Chem Soc Rev 20:20
Zheng YN, Zheng H, Li T, Wei WT (2021) Recent advances in copper-catalyzed C−N bond formation involving N-centered radicals. Chemsuschem 20:20
Collet F, Lescot C, Dauban P (2011) Catalytic C–H amination: the stereoselectivity issue. Chem Soc Rev. https://doi.org/10.1039/c0cs00095g
Jeffrey JL, Sarpong R (2013) Intramolecular C(sp3)–H amination. Chem Sci. https://doi.org/10.1039/c3sc51420j
Lu Z, Ma S (2008) Metal-catalyzed enantioselective allylation in asymmetric synthesis. Angew Chem Int Ed 20:25
Barker TJ, Jarvo ER (2011) Developments in transition-metal-catalyzed reactions using electrophilic nitrogen sources. Synthesis (Stuttg) 20:25
Wang C (2020) Development of transition-metal-catalysed cross-coupling reactions through ammonium C–N bond cleavage. Chem Pharm Bull 25:25
Goodbrand HB, Hu NX (1999) Ligand-accelerated catalysis of the Ullmann condensation: application to hole-conducting triarylamines. J Org Chem. https://doi.org/10.1021/jo981804o
Strieter ER, Blackmond DG, Buchwald SL (2005) The role of chelating diamine ligands in the Goldberg reaction: a kinetic study on the copper-catalyzed amidation of aryl iodides. J Am Chem Soc. https://doi.org/10.1021/ja050120c
Klapars A, Huang X, Buchwald SL (2002) A general and efficient copper catalyst for the amidation of aryl halides. J Am Chem Soc. https://doi.org/10.1021/ja0260465
Bruno NC, Tudge MT, Buchwald SL (2013) Design and preparation of new palladium precatalysts for C-C and C–N cross-coupling reactions. Chem Sci. https://doi.org/10.1039/c2sc20903a
Roizen JL, Harvey ME, Du BJ (2012) Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C–H bonds. Acc Chem Res. https://doi.org/10.1021/ar200318q
Simon RC, Grischek B, Zepeck F et al (2012) Regio- and stereoselective monoamination of diketones without protecting groups. Angew Chem Int Ed. https://doi.org/10.1002/anie.201202375
Simon RC, Grischek B, Zepeck F et al (2012) Regio- and stereoselective monoamination of diketones without protecting groups. Angew Chem. https://doi.org/10.1002/ange.201202375
Campbell AN, Stahl SS (2012) Overcoming the ‘oxidant problem’: strategies to use O2 as the oxidant in organometallic C–H oxidation reactions catalyzed by Pd (and Cu). Acc Chem Res. https://doi.org/10.1021/ar2002045
Gephart RT, Warren TH (2012) Copper-catalyzed sp3 C-H amination. Organometallics 25:24
Louillat ML, Patureau FW (2014) Oxidative C-H amination reactions. Chem Soc Rev 25:45
Yan X, Yang X, ** C (2014) Recent progress in copper-catalyzed electrophilic amination. Catal Sci Technol 20:25
Erdik E, Ay M (1989) Electrophilic amination of carbanions. Chem Rev. https://doi.org/10.1021/cr00098a014
Daşkapan T (2011) Synthesis of amines by the electrophilic amination of organomagnesium,- zinc,-copper, and-lithium reagents. ARKIVOC. https://doi.org/10.3998/ark.5550190.0012.520
Dong X, Liu Q, Dong Y, Liu H (2017) Transition-metal-catalyzed electrophilic amination: application of O-benzoylhydroxylamines in the construction of the C−N bond. Chem A Eur J 20:25
Berman AM, Johnson JS (2004) Copper-catalyzed electrophilic amination of diorganozinc reagents. J Am Chem Soc. https://doi.org/10.1021/ja049474e
Cho SH, Kim JY, Kwak J, Chang S (2011) Recent advances in the transition metal-catalyzed twofold oxidative C–H bond activation strategy for C–C and C–N bond formation. Chem Soc Rev. https://doi.org/10.1039/c1cs15082k
Bariwal J, Van Der Eycken E (2013) C-N bond forming cross-coupling reactions: an overview. Chem Soc Rev 20:525
Beccalli EM, Broggini G, Martinelli M, Sottocornola S (2007) C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents. Chem Rev 25:25
Luo J, Wei WT (2018) Recent Advances in the construction of C–N bonds through coupling reactions between carbon radicals and nitrogen radicals. Adv Synth Catal 25:45
Campbell MJ, Johnson JS (2007) Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol. Org Lett. https://doi.org/10.1021/ol0702829
McDonald SL, Wang Q (2014) Copper-catalyzed α-amination of phosphonates and phosphine oxides: a direct approach to α-amino phosphonic acids and derivatives. Angew Chem. https://doi.org/10.1002/ange.201308890
Rucker RP, Whittaker AM, Dang H, Lalic G (2012) Synthesis of hindered anilines: copper-catalyzed electrophilic amination of aryl boronic esters. Angew Chem Int Ed. https://doi.org/10.1002/anie.201200480
Müller TE, Hultzsch KC, Yus M et al (2008) Hydroamination: direct addition of amines to alkenes and alkynes. Chem Rev. https://doi.org/10.1021/cr0306788
Gooßen LJ, Huang L, Arndt M et al (2015) Late transition metal-catalyzed hydroamination and hydroamidation. Chem Rev 25:25
Johns AM, Sakai N, Ridder A, Hartwig JF (2006) Direct measurement of the thermodynamics of vinylarene hydroamination. J Am Chem Soc. https://doi.org/10.1021/ja062773e
Müller TE, Beller M (1998) Metal-initiated amination of alkenes and alkynes. Chem Rev. https://doi.org/10.1021/cr960433d
Seebach D, Corey EJ (1975) Generation and synthetic applications of 2-lithio-1,3-dithianes. J Org Chem. https://doi.org/10.1021/jo00890a018
Seebach D (1979) Methods of reactivity umpolung. Angew Chem Int Ed English 25:25
Miki Y, Hirano K, Satoh T, Miura M (2013) Copper-catalyzed intermolecular regioselective hydroamination of styrenes with polymethylhydrosiloxane and hydroxylamines. Angew Chem Int Ed. https://doi.org/10.1002/anie.201304365
Zhu S, Niljianskul N, Buchwald SL (2013) Enantio- and regioselective CuH-catalyzed hydroamination of alkenes. J Am Chem Soc. https://doi.org/10.1021/ja4092819
Miki Y, Hirano K, Satoh T, Miura M (2014) Copper-catalyzed enantioselective formal hydroamination of oxa- and azabicyclic alkenes with hydrosilanes and hydroxylamines. Org Lett. https://doi.org/10.1021/ol5003219
Niljianskul N, Zhu S, Buchwald SL (2015) Enantioselective synthesis of α-aminosilanes by copper-catalyzed hydroamination of vinylsilanes. Angew Chem. https://doi.org/10.1002/ange.201410326
Shi SL, Buchwald SL (2015) Copper-catalysed selective hydroamination reactions of alkynes. Nat Chem. https://doi.org/10.1038/nchem.2131
Niu D, Buchwald SL (2015) Design of modified amine transfer reagents allows the synthesis of α-chiral secondary amines via CuH-catalyzed hydroamination. J Am Chem Soc. https://doi.org/10.1021/jacs.5b05446
Ichikawa S, Zhu S, Buchwald SL (2018) A modified system for the synthesis of enantioenriched N-arylamines through copper-catalyzed hydroamination. Angew Chem Int Ed. https://doi.org/10.1002/anie.201803026
Feng S, Hao H, Liu P, Buchwald SL (2020) Diastereo- and enantioselective CuH-catalyzed hydroamination of strained trisubstituted alkenes. ACS Catal. https://doi.org/10.1021/acscatal.9b04871
Ichikawa S, Buchwald SL (2019) Asymmetric synthesis of γ-amino alcohols by copper-catalyzed hydroamination. Org Lett. https://doi.org/10.1021/acs.orglett.9b03356
Takata T, Nishikawa D, Hirano K, Miura M (2018) Synthesis of α-aminophosphines by copper-catalyzed regioselective hydroamination of vinylphosphines. Chem A Eur J. https://doi.org/10.1002/chem.201802491
Yang Q, Li S, Wang J (2020) Asymmetric synthesis of chiral chromanes by copper-catalyzed hydroamination of 2H-chromenes. ChemCatChem. https://doi.org/10.1002/cctc.202000601
Takata T, Hirano K, Miura M (2019) Synthesis of α-trifluoromethylamines by Cu-catalyzed regio- and enantioselective hydroamination of 1-trifluoromethylalkenes. Org Lett. https://doi.org/10.1021/acs.orglett.9b01471
Nishino S, Miura M, Hirano K (2021) An umpolung-enabled copper-catalysed regioselective hydroamination approach to α-amino acids. Chem Sci. https://doi.org/10.1039/d1sc03692k
Jeon J, Lee C, Seo H, Hong S (2020) NiH-catalyzed proximal-selective hydroamination of unactivated alkenes. J Am Chem Soc. https://doi.org/10.1021/jacs.0c10333
Lee C, Seo H, Jeon J, Hong S (2021) γ-Selective C(sp3)–H amination via controlled migratory hydroamination. Nat Commun. https://doi.org/10.1038/s41467-021-25696-z
Lee C, Kang H-J, Seo H, Hong S (2022) Nickel-catalyzed regio- and enantioselective hydroamination of unactivated alkenes using carbonyl directing groups. J Am Chem Soc 144:9091–9100. https://doi.org/10.1021/jacs.2c02343
Yang D, Huang H, Zhang H et al (2021) Regioselective intermolecular hydroamination of unactivated alkenes: ‘co-H’ enabled remote functionalization. ACS Catal. https://doi.org/10.1021/acscatal.1c00625
Matsuda N, Hirano K, Satoh T, Miura M (2013) Regioselective and stereospecific copper-catalyzed aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines. J Am Chem Soc 20:25. https://doi.org/10.1021/ja4007645
Sakae R, Matsuda N, Hirano K et al (2014) Highly stereoselective synthesis of (borylmethyl)cyclopropylamines by copper-catalyzed aminoboration of methylenecyclopropanes. Org Lett. https://doi.org/10.1021/ol5001507
Sakae R, Hirano K, Satoh T, Miura M (2015) Copper-catalyzed stereoselective aminoboration of bicyclic alkenes. Angew Chem. https://doi.org/10.1002/ange.201409104
Sakae R, Hirano K, Miura M (2015) Ligand-controlled regiodivergent Cu-catalyzed aminoboration of unactivated terminal alkenes. J Am Chem Soc. https://doi.org/10.1021/jacs.5b02775
Kato K, Hirano K, Miura M (2017) Copper/bisphosphine catalysts in the internally borylative aminoboration of unactivated terminal alkenes with bis(pinacolato)diboron. J Org Chem. https://doi.org/10.1021/acs.joc.7b01874
Kato K, Hirano K, Miura M (2018) Copper-catalyzed regio- and enantioselective aminoboration of unactivated terminal alkenes. Chem A Eur J. https://doi.org/10.1002/chem.201801070
Gao DW, Gao Y, Shao H et al (2020) Cascade CuH-catalysed conversion of alkynes into enantioenriched 1,1-disubstituted products. Nat Catal. https://doi.org/10.1038/s41929-019-0384-6
Hemric BN, Chen AW, Wang Q (2019) Copper-catalyzed 1,2-amino oxygenation of 1,3-dienes: a chemo-, regio-, and site-selective three-component reaction with o-acylhydroxylamines and carboxylic acids. ACS Catal. https://doi.org/10.1021/acscatal.9b03076
Li Z, Zhang M, Zhang Y et al (2019) Multicomponent cyclopropane synthesis enabled by Cu-catalyzed cyclopropene carbometalation with organoboron reagent: enantioselective modular access to polysubstituted 2-arylcyclopropylamines. Org Lett. https://doi.org/10.1021/acs.orglett.9b01650
Zhang Y, Li Y, Zhou W et al (2020) Assembly of polysubstituted chiral cyclopropylamines via highly enantioselective Cu-catalyzed three-component cyclopropene alkenylamination. Chem Commun. https://doi.org/10.1039/d0cc01060j
Simaan M, Marek I (2018) Asymmetric catalytic preparation of polysubstituted cyclopropanol and cyclopropylamine derivatives. Angew Chem Int Ed. https://doi.org/10.1002/anie.201710707
Kwon Y, Wang Q (2020) Copper-catalyzed 1,2-aminocyanation of unactivated alkenes via cyano migration. Org Lett. https://doi.org/10.1021/acs.orglett.0c01217
Kwon Y, Zhang W, Wang Q (2021) Copper-catalyzed aminoheteroarylation of unactivated alkenes through distal heteroaryl migration. ACS Catal. https://doi.org/10.1021/acscatal.1c01001
Shen G, Zhao L, Wang Y, Zhang T (2016) Room temperature copper-catalyzed oxidative amidation of terminal alkynes for the synthesis of α-ketoamides using: O-benzoyl hydroxylamines as aminating reagent and oxidant. RSC Adv. https://doi.org/10.1039/c6ra15219h
Van Der Puyl VA, Derosa J, Engle KM (2019) Directed, nickel-catalyzed umpolung 1,2-carboamination of alkenyl carbonyl compounds. ACS Catal. https://doi.org/10.1021/acscatal.8b04516
**e L, Wang S, Zhang L et al (2021) Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes. Nat Commun. https://doi.org/10.1038/s41467-021-26527-x
Brown HC, Heydkamp WR, Breuer E, Murphy WS (1964) The Reaction of organoboranes with chloramine and with hydroxylamine-O-sulfonic acid. A convenient synthesis of amines from olefins via hydroboration. J Am Chem Soc. https://doi.org/10.1021/ja01071a036
Brown HC, Kim KW, Srebnik M, Bakthan S (1987) Organoboranes for synthesis. 7. An improved general synthesis of primary amines from alkenes via hydroboration-organoborane chemistry. Tetrahedron. https://doi.org/10.1016/S0040-4020(01)83445-1
Rangaishenvi MV, Brown HC, Singaram B (1991) Chiral synthesis via organoboranes. 30. Facile synthesis, by the Matteson asymmetric homologation procedure, of α-methyl boronic acids not available from asymmetric hydroboration and their conversion into the corresponding aldehydes, ketones, carboxylic A. J Org Chem 20:25. https://doi.org/10.1021/jo00010a022
Matsuda N, Hirano K, Satoh T, Miura M (2012) Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines. Angew Chem 25:25. https://doi.org/10.1002/ange.201108773
Rucker RP, Whittaker AM, Dang H, Lalic G (2012) Synthesis of hindered anilines: copper-catalyzed electrophilic amination of aryl boronic esters. Angew Chem. https://doi.org/10.1002/ange.201200480
Rucker RP, Whittaker AM, Dang H, Lalic G (2012) Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes. J Am Chem Soc. https://doi.org/10.1021/ja3023829
**ao Q, Tian L, Tan R et al (2012) Transition-metal-free electrophilic amination of arylboroxines. Org Lett. https://doi.org/10.1021/ol301912a
Mlynarski SN, Karns AS, Morken JP (2012) Direct stereospecific amination of alkyl and aryl pinacol boronates. J Am Chem Soc. https://doi.org/10.1021/ja305448w
Nishikawa D, Hirano K, Miura M (2016) Copper-catalyzed regio- and stereoselective aminoboration of alkenylboronates. Org Lett. https://doi.org/10.1021/acs.orglett.6b02338
Zhu H, Shen Y, Deng Q et al (2017) One-pot bimetallic Pd/Cu-catalyzed synthesis of sulfonamides from boronic acids, DABSO and O-benzoyl hydroxylamines. Chem Asian J 25:25. https://doi.org/10.1002/asia.201601732
Chen Y-H, Graßl S, Knochel P (2018) Cobalt-katalysierte elektrophile aminierung von aryl- und heteroarylzinkpivalaten mit N-hydroxylaminbenzoaten. Angew Chem. https://doi.org/10.1002/ange.201710931
Graßl S, Chen YH, Hamze C et al (2019) Late stage functionalization of secondary amines via a cobalt-catalyzed electrophilic amination of organozinc reagents. Org Lett. https://doi.org/10.1021/acs.orglett.8b03787
Yoon H, Kim Y, Lee Y (2017) Cu-Catalyzed electrophilic amination of internal alkynes via hydroalumination. Org Biomol Chem. https://doi.org/10.1039/c6ob02606k
Zhang Q, Hitoshio K, Saito H et al (2020) Copper-catalyzed electrophilic amination of alkoxyarylsilanes. Eur J Org Chem. https://doi.org/10.1002/ejoc.202000562
Lee S, Lee Y (2019) Copper-catalyzed electrophilic amination of benzoxazoles via magnesation. Eur J Org Chem. https://doi.org/10.1002/ejoc.201900335
Wang W, Peng X, Wei F et al (2016) Copper(I)-catalyzed interrupted click reaction: synthesis of diverse 5-hetero-functionalized triazoles. Angew Chem. https://doi.org/10.1002/ange.201509124
Hemric BN, Chen AW, Wang Q (2019) Copper-catalyzed modular amino oxygenation of alkenes: access to diverse 1,2-amino oxygen-containing skeletons. J Org Chem. https://doi.org/10.1021/acs.joc.8b02885
Yang Z, Jiang K, Chen YC, Wei Y (2019) Copper-catalyzed dihydroquinolinone synthesis from isocyanides and O-benzoyl hydroxylamines. J Org Chem. https://doi.org/10.1021/acs.joc.9b00262
Peterson LJ, Kirsch JK, Wolfe JP (2018) Pd-catalyzed alkene diamination reactions of nitrogen electrophiles: synthesis of cyclic guanidines and ureas bearing dialkylaminomethyl groups. Org Lett. https://doi.org/10.1021/acs.orglett.8b01289
Yu H, Li Z, Bolm C (2018) Copper-catalyzed transsulfinamidation of sulfinamides as a key step in the preparation of sulfonamides and sulfonimidamides. Angew Chem. https://doi.org/10.1002/ange.201810548
Zhu H, Shen Y, Deng Q et al (2017) Ligand-free Pd/Cu-catalyzed aminosulfonylation of aryl iodides for direct sulfonamide syntheses. Asian J Org Chem. https://doi.org/10.1002/ajoc.201700350
Zhang W, Wang C, Wang Q (2020) Copper-catalyzed decarboxylative functionalization of conjugated β, Γ-unsaturated carboxylic acids. ACS Catal 25:45. https://doi.org/10.1021/acscatal.0c03621
Dai Q, Zhang J (2018) Direct synthesis of sulfinamides by the copper-catalyzed electrophilic amidation of sulfenate anions. Adv Synth Catal. https://doi.org/10.1002/adsc.201701510
Nguyen VT, Haug GC, Nguyen VD et al (2021) Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides. Chem Sci. https://doi.org/10.1039/d1sc01389k
Begam HM, Choudhury R, Behera A, Jana R (2019) Copper-catalyzed electrophilic ortho C(sp2)-H amination of aryl amines: dramatic reactivity of bicyclic system. Org Lett. https://doi.org/10.1021/acs.orglett.9b01546
Yao ZL, Wang L, Shao NQ et al (2019) Copper-catalyzed ortho-selective dearomative C–N coupling of simple phenols with O-benzoylhydroxylamines. ACS Catal. https://doi.org/10.1021/acscatal.9b01317
Li M, Wang DH (2021) Copper-catalyzed 3-positional amination of 2-azulenols with O-benzoylhydroxylamines. Org Lett. https://doi.org/10.1021/acs.orglett.1c02132
Rao WH, Li Q, Jiang LL et al (2021) Copper-catalyzed intermolecular C(sp2)-H amination with electrophilic O-benzoyl hydroxylamines. J Org Chem. https://doi.org/10.1021/acs.joc.1c01229
Catellani M, Frignani F, Rangoni A (1997) A complex catalytic cycle leading to a regioselective synthesis of O, O-disubstituted vinylarenes. Angew Chem (Int Ed English). https://doi.org/10.1002/anie.199701191
Motti E, Ippomei G, Deledda S, Catellani M (2003) Synthesis of selectively substituted ortho-vinylbiphenyls by palladium-catalysed reaction of ortho-substituted aryl iodides with olefins. Synthesis (Stuttg). https://doi.org/10.1055/s-2003-42441
Martins A, Mariampillai B, Lautens M (2010) Synthesis in the key of Catellani: norbornene-mediated ortho C–H functionalization. Top Curr Chem 25:25
Ferraccioli R (2013) Palladium-catalyzed synthesis of carbo- and heterocycles through norbornene-mediated ortho C–H functionalization. Synth. https://doi.org/10.1055/s-0032-1318218
Ye J, Lautens M (2015) Palladium-catalysed norbornene-mediated C-H functionalization of arenes. Nat Chem 20:25
Della Ca N, Fontana M, Motti E, Catellani M (2016) Pd/norbornene: a winning combination for selective aromatic functionalization via C–H bond activation. Acc Chem Res. https://doi.org/10.1021/acs.accounts.6b00165
Dong Z, Dong G (2013) Ortho vs ipso: site-selective pd and norbornene-catalyzed arene C–H amination using aryl halides. J Am Chem Soc. https://doi.org/10.1021/ja410823e
Chen ZY, Ye CQ, Zhu H et al (2014) Palladium/norbornene-mediated tandem C–H amination/C-I alkenylation reaction of aryl iodides with secondary cyclic O-benzoyl hydroxylamines and activated terminal olefins. Chem A Eur J. https://doi.org/10.1002/chem.201400084
Ye C, Zhu H, Chen Z (2014) Synthesis of biaryl tertiary amines through Pd/norbornene joint catalysis in a remote C–H amination/Suzuki coupling reaction. J Org Chem. https://doi.org/10.1021/jo501544h
Zhou PX, Ye YY, Ma JW et al (2014) Palladium-catalyzed/norbornene-mediated ortho-amination/N-tosylhydrazone insertion reaction: an approach to the synthesis of ortho-aminated vinylarenes. J Org Chem. https://doi.org/10.1021/jo501125b
Pan S, Ma X, Zhong D et al (2015) Palladium-catalyzed one-pot consecutive amination and Sonogashira coupling for selective synthesis of 2-alkynylanilines. Adv Synth Catal. https://doi.org/10.1002/adsc.201500381
Shi H, Babinski DJ, Ritter T (2015) Modular C–H functionalization cascade of aryl iodides. J Am Chem Soc. https://doi.org/10.1021/jacs.5b01082
Sun F, Gu Z (2015) Decarboxylative alkynyl termination of palladium-catalyzed Catellani reaction: a facile synthesis of α-alkynyl anilines via ortho C–H amination and alkynylation. Org Lett. https://doi.org/10.1021/acs.orglett.5b00830
Wang J, Gu Z (2016) Synthesis of 2-(1-alkoxyvinyl)anilines by palladium/norbornene-catalyzed amination followed by termination with vinyl ethers. Adv Synth Catal. https://doi.org/10.1002/adsc.201600339
Majhi B, Ranu BC (2016) Palladium-catalyzed norbornene-mediated tandem ortho-C–H-amination/ipso-C-I-cyanation of iodoarenes: regiospecific synthesis of 2-aminobenzonitrile. Org Lett. https://doi.org/10.1021/acs.orglett.6b02113
Luo B, Gao JM, Lautens M (2016) Palladium-catalyzed norbornene-mediated tandem amination/cyanation reaction: a method for the synthesis of ortho-aminated benzonitriles. Org Lett. https://doi.org/10.1021/acs.orglett.6b02249
Whyte A, Olson ME, Lautens M (2018) Palladium-catalyzed, norbornene-mediated, ortho-amination ipso-amidation: sequential C–N bond formation. Org Lett. https://doi.org/10.1021/acs.orglett.7b03577
Fan L, Liu J, Bai L et al (2017) Rapid assembly of diversely functionalized spiroindenes by a three-component palladium-catalyzed C−H amination/phenol dearomatization domino reaction. Angew Chem. https://doi.org/10.1002/ange.201708310
Wang J, Li R, Dong Z et al (2018) Complementary site-selectivity in arene functionalization enabled by overcoming the ortho constraint in palladium/norbornene catalysis. Nat Chem. https://doi.org/10.1038/s41557-018-0074-z
Dong Z, Lu G, Wang J et al (2018) Modular ipso/ortho difunctionalization of aryl bromides via palladium/norbornene cooperative catalysis. J Am Chem Soc. https://doi.org/10.1021/jacs.8b04153
Zhang BS, Li Y, An Y et al (2018) Carboxylate ligand-exchanged amination/C(sp3)-H arylation reaction via Pd/norbornene cooperative catalysis. ACS Catal. https://doi.org/10.1021/acscatal.8b04163
Chen S, Wang P, Cheng HG et al (2019) Redox-neutral: ortho -C–H amination of pinacol arylborates via palladium(ii)/norbornene catalysis for aniline synthesis. Chem Sci. https://doi.org/10.1039/c9sc02759a
Abel-Snape X, Whyte A, Lautens M (2020) Synthesis of aminated phenanthridinones via palladium/norbornene catalysis. Org Lett. https://doi.org/10.1021/acs.orglett.0c02850
An Y, Zhang BS, Zhang Z et al (2020) A carboxylate-assisted amination/unactivated C(sp2)-H arylation reaction via palladium/norbornene cooperative catalysis. Chem Commun 25:5
Chen Y, Lv W, Ba D et al (2020) Palladium-catalyzed chemoselective synthesis of 2-aminocinnamyl esters via sequential amination and olefination of aryl iodides. J Org Chem. https://doi.org/10.1021/acs.joc.0c01695
Zhang BS, Li Y, Gou XY et al (2020) DMAP and PivOH-promoted amination/allenization reaction. Chem Commun. https://doi.org/10.1039/d0cc03749d
Wang CT, Li M, Ding YN et al (2021) Alkylation-terminated Catellani reactions by cyclobutanol C-C cleavage. Org Lett. https://doi.org/10.1021/acs.orglett.0c04018
Zhao S, Han S, Du G et al (2021) Acid-promoted expeditious syntheses of aminated dibenzosultams via palladium/norbornene cooperatively catalysed C−H amination/arylation. Adv Synth Catal. https://doi.org/10.1002/adsc.202001413
Zheng N, Liu C, Ding YN et al (2020) Copper-catalyzed three-component redox-neutral ring opening of benzothiazoles to 1-amino-N-(2-(phenylthio)phenyl)methanimine. J Org Chem. https://doi.org/10.1021/acs.joc.9b03489
Acknowledgements
The authors are thankful to the Discipline of Pharmaceutical Sciences, College of Health Sciences, University of Kwa-Zulu Natal (UKZN), Durban, South Africa, for providing all the necessary facilities. R.K. gratefully acknowledges National Research Foundation-South Africa for funding this project (Grant No. 129247).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The reported work is acknowledged/cited, with no potential conflicts of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Mohite, S.B., Bera, M., Kumar, V. et al. O-Benzoylhydroxylamines: A Versatile Electrophilic Aminating Reagent for Transition Metal-Catalyzed C–N Bond-Forming Reactions. Top Curr Chem (Z) 381, 4 (2023). https://doi.org/10.1007/s41061-022-00414-5
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s41061-022-00414-5