Synthesis 2020; 52(19): 2807-2820
DOI: 10.1055/s-0040-1707885
short review
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed anti-Selective Alkyne Functionalization Reactions

Sydney E. Bottcher
,
Lauren E. Hutchinson
,
Samford University, Department of Chemistry and Biochemistry, 800 Lakeshore Dr., Birmingham, AL 35229, USA   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 30 March 2020

Accepted after revision: 19 May 2020

Publication Date:
22 June 2020 (online)


Abstract

Nickel-catalyzed anti-selective alkyne functionalization reactions are reviewed with an emphasis on the mechanisms that lead to their observed stereoselectivity. Since the isomerization of alkenylnickel species plays a key role in a large number of these reactions, the potential mechanisms for these processes are also described in detail.

1 Introduction

2 anti-Selective Hydroarylation

3 anti-Selective Carboborylation

4 anti-Selective Dicarbofunctionalization

4.1 Carbocyanative Cyclization

4.2 Cyclization with Aryl Donors

4.3 Cyclization with CO2

4.4 Intermolecular Dicarbofunctionalization

5 anti-Selective Carbosulfonylation

6 Alkenylnickel Isomerization

7 Conclusions

 
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