Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

Shuangqiu Gao; Lili Shi; Le Chang; Binglin Wang; Junkai Fu

doi:10.1055/s-0040-1705966

Synthesis, Table of Contents

Synthesis 2021; 53(05): 861-878
DOI: 10.1055/s-0040-1705966

short review

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

Shuangqiu Gao

^aJilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China Email: fujk109@nenu.edu.cn

,

Lili Shi∗

^bState Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China Email: shill@pkusz.edu.cn

,

Le Chang

^cWuXi AppTec (Wuhan) Co. Ltd., Wuhan East Lake High-tech Development Zone, Wuhan 430075, P. R. of China

,

Binglin Wang

^cWuXi AppTec (Wuhan) Co. Ltd., Wuhan East Lake High-tech Development Zone, Wuhan 430075, P. R. of China

,

Junkai Fu ∗

^aJilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China Email: fujk109@nenu.edu.cn

^bState Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China Email: shill@pkusz.edu.cn

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Abstract

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Abstract

The Mizoroki–Heck reaction is considered as one of the most ingenious and widely used methods for constructing C–C bonds. This reaction mainly focuses on activated olefins (styrenes, acrylates, or vinyl ethers) and aryl/vinyl (pseudo) halides. In comparison, the studies on unactivated alkenes and alkyl electrophiles are far less due to the low reactivity, poor selectivity, as well as competitive β-H elimination. In the past years, a growing interest has thus been devoted and significant breakthroughs have been achieved in the employment of unactivated alkenes and alkyl electrophiles as the reaction components, and this type of coupling is called as Heck-type or Heck-like reaction, which distinguishes from the traditional Heck reaction. Herein, we give a brief summary on Heck-type reaction between unactivated alkenes and alkyl electrophlies, covering its initial work, recent advancements, and mechanistic discussions.

1 Introduction

2 Intramolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

2.1 Cobalt-Catalyzed Intramolecular Heck-Type Reaction

2.2 Palladium-Catalyzed Intramolecular Heck-Type Reaction

2.3 Nickel-Catalyzed Intramolecular Heck-Type Reaction

2.4 Photocatalysis and Multimetallic Protocol for Intramolecular Heck-Type Reaction

3 Intermolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

3.1 Electrophilic Trifluoromethylating Reagent as Reaction Partners

3.2 Alkyl Electrophiles as Reaction Partners

4 Oxidative Heck-Type Reaction of Unactivated Alkenes and Alkyl Radicals

5 Conclusions and Outlook

Key words

Heck reaction - unactivated alkenes - alkyl electrophiles - carbon–carbon bond formation - radical chemistry

Full Text

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