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DOI: 10.1055/a-2111-9629
Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction
A.P.P. thanks the Engineering and Physical Sciences Research Council (EPSRC) for funding (EP/W02151X/1 and EP/Y00146X/1). R.L.M. would like to thank the EPSRC for a research fellowship (EP/R026912/1). J.P.G., L.W., L.Y. and A.P.P. thank the University of Leicester for generous support. L.Y. thanks the China Scholarship Council for funding. S.A.E., R.L.M. and L.C.M. gratefully acknowledge the School of Chemistry, Cardiff University for generous support. S.A.E. thanks the British Council and the Egyptian Cultural Affairs and Missions Sector for a Ph.D. studentship through the Newton-Mosharafa Fund.
Dedicated to 60 years of Donald Matteson’s boron homologation
Abstract
C–H functionalization is widely regarded as an important area in the development of synthetic methodology, enabling the design of more time- and atom-efficient syntheses. The ability of electron-deficient organoboranes to mediate hydride abstraction from α-amino C–H bonds is therefore of great interest, as the reactive iminium and hydridoborate moieties generated are able to participate in a range of synthetically useful transformations. In this review, we cover the recent advances made in organoborane-mediated hydride abstraction, and focus on the catalytic applications of electron-deficient boranes in α- or β-functionalization, α,β-difunctionalization, and the dehydrogenation of amines.
1 Introduction
2 α-Functionalization of Amines
3 β-Functionalization of Amines
4 α,β-Difunctionalization of Amines
5 Dehydrogenation of Amines
6 Summary and Future Prospects
Publication History
Received: 31 May 2023
Accepted after revision: 14 June 2023
Accepted Manuscript online:
16 June 2023
Article published online:
04 September 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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