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N-Alkylation by Hydrogen Autotransfer Reactions

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An Erratum to this article was published on 10 May 2016

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Abstract

Owing to the importance of amine/amide derivatives in all fields of chemistry, and also the green and environmentally benign features of using alcohols as alkylating reagents, the relatively high atom economic dehydrative N-alkylation reactions of amines/amides with alcohols through hydrogen autotransfer processes have received much attention and have developed rapidly in recent decades. Various efficient homogeneous and heterogeneous transition metal catalysts, nano materials, electrochemical methods, biomimetic methods, asymmetric N-alkylation reactions, aerobic oxidative methods, and even certain transition metal-free, catalyst-free, or autocatalyzed methods, have also been developed in recent years. With a brief introduction to the background and developments in this area of research, this chapter focuses mainly on recent progress and technical and conceptual advances contributing to the development of this research in the last decade. In addition to mainstream research on homogeneous and heterogeneous transition metal-catalyzed reactions, possible mechanistic routes for hydrogen transfer and alcohol activation, which are key processes in N-alkylation reactions but seldom discussed in the past, the recent reports on computational mechanistic studies of the N-alkylation reactions, and the newly emerged N-alkylation methods based on novel alcohol activation protocols such as air-promoted reactions and transition metal-free methods, are also reviewed in this chapter. Problems and bottlenecks that remained to be solved in the field, and promising new research that deserves greater future attention and effort, are also reviewed and discussed.

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  • 10 May 2016

    An erratum to this article has been published.

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Acknowledgments

We thank ZJNSF for Distinguished Young Scholars (LR14B020002), NNSFC (51502174), 580 Overseas Talents Program of Wenzhou, and Science and Technology Project of Shenzhen (JCYJ20150324141711616) for financial support.

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  1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang, 325035, China

    **antao Ma & Qing Xu

  2. SZU-NUS Collaborative Innovation Center for Optoelectronic Science and Technology, Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Optoelectronic Engineering, Shenzhen University, Shenzhen, 518060, China

    **antao Ma & Chenliang Su

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  1. **antao Ma
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Correspondence to Qing Xu.

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This article is part of the Topical Collection “Hydrogen Transfer Reactions”; edited by Gabriela Guillena, Diego J. Ramón.

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Ma, X., Su, C. & Xu, Q. N-Alkylation by Hydrogen Autotransfer Reactions. Top Curr Chem (Z) 374, 27 (2016). https://doi.org/10.1007/s41061-016-0027-1

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