Synthesis 2020; 52(07): 979-992
DOI: 10.1055/s-0039-1690807
short review
© Georg Thieme Verlag Stuttgart · New York

Ni-Catalyzed Reductive Difunctionalization of Alkenes

Yuanyuan Ping
,
Grateful for financial support from the ‘1000-Youth Talents Plan’, National­ Natural Science Foundation of China (No. 21702149), Fundamental Research Funds for the Central Universities (2042018kf0012), and Wuhan University.
Further Information

Publication History

Received: 16 December 2019

Accepted after revision: 09 January 2020

Publication Date:
19 February 2020 (online)


Abstract

Alkene difunctionalization represents one of the most efficient methods to synthesize highly functionalized molecules from simple and readily available starting materials. In contrast to the well-established redox-neutral alkene difunctionalization reactions, reductive alkene difunctionalization, which simultaneously introduces two electrophiles on both sides of the double bond, has been much less developed, especially in enantioselective manner. This review summarizes recent advances in the nickel-catalyzed reductive difunctionalization of alkenes and highlights the enantioselective transformations.

1 Introduction

2 Nickel-Catalyzed Racemic Reductive Difunctionalization of Alkenes

3 Nickel-Catalyzed Enantioselective Reductive Difunctionalization of Alkenes

3.1 Diarylation of Alkenes

3.2 Aryl-alkenylation of Alkenes

3.3 Aryl-monofluoroalkenylation of Alkenes

3.4 Reductive Cyclization/Coupling with Alkynyl Bromides or Asymmetric Internal Alkynes

3.5 Aryl-alkylation of Alkenes

3.6 Aryl-amination of Alkenes

4 Summary and Outlook

 
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