Synlett
DOI: 10.1055/s-0036-1589077
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© Georg Thieme Verlag Stuttgart · New York

Regioselective Hydroamination Using a Directed Nucleopalladation/Protodepalladation Strategy

John A. Gurak Jr, Keary M. Engle*
  • Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA   Email: keary@scripps.edu
We gratefully acknowledge TSRI and Pfizer, Inc. for financial support, as well as the Donald E. and Delia B. Baxter Foundation and the National Science Foundation (NSF/DGE-1346837) for predoctoral fellowships (J.A.G.)
Further Information

Publication History

Received: 15 May 2017

Accepted after revision: 21 June 2017

Publication Date:
02 August 2017 (eFirst)

Abstract

Alkene hydroamination is an attractive approach for converting alkenes into structurally complex amine products. Several different strategies have been pursued over the past few decades to achieve this historically challenging reaction. One of the key issues associated with this transformation is control of regioselectivity, which is particularly difficult for internal non-conjugated alkenes. Our group has recently found success using a removable bidentate auxiliary to control regioselectivity and stabilize the key nucleopalladated intermediate in a palladium(II)-catalyzed alkene hydroamination with N–H nucleophiles. This article describes the historical context for this work, the underlying conceptual logic, our results to date, and the future outlook.