Nickel-Catalyzed Highly Atom-Economical C–C Coupling Reactions with π Components

Li-Jun Xiao; Meng-Chun Ye; Qi-Lin Zhou

doi:10.1055/s-0037-1610410

Synlett, Table of Contents

CC BY ND NC 4.0 · Synlett 2019; 30(04): 361-369
DOI: 10.1055/s-0037-1610410

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Nickel-Catalyzed Highly Atom-Economical C–C Coupling Reactions with π Components

Li-Jun Xiao

^aState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China Email: mcye@nankai.edu.cn

,

Meng-Chun Ye*

^aState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China Email: mcye@nankai.edu.cn

,

Qi-Lin Zhou *

^aState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China Email: mcye@nankai.edu.cn

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China Email: qlzhou@nankai.edu.cn

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Abstract

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Published as part of the 30 Years SYNLETT – Pearl Anniversary Issue

Abstract

This account describes our latest advances in the field of nickel(0)-catalyzed hydrofunctionalization of π components. All reactions proceed either through internal hydride transfer or by using an external proton as the hydride source, thereby eliminating the use of stoichiometric amounts of reductants or oxidants. These nickel-catalyzed atom-economical coupling reactions demonstrate that nickel not only is an inexpensive metal catalyst, but also possesses unique and versatile catalytic abilities. Current limitations and the outlook of these reactions are also discussed.

1 Introduction

2 Nickel(0)-Catalyzed Hydroacylation of Styrenes with Simple Aldehydes

3 Nickel(0)-Catalyzed Hydroalkenylation of Imines and Aldehydes with Alkenes

4 Nickel(0)-Catalyzed Hydroarylation of Styrenes and 1,3-Dienes with Organoboronic Derivatives

5 Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones

6 Summary and Outlook

Key words

alkenes - ketones - nickel - aldehydes - imines - coupling

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References

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