中文   |   English   |   Email Alert

Palladium Catalyzed Heck-Type Reaction of Organic Halides and Alkyl-Alkynes

Chenghao Zhu , Junliang Zhang

Progress in Chemistry ›› 2020, Vol. 32 ›› Issue (11) : 1745 -1752.

PDF
Progress in Chemistry ›› 2020, Vol. 32 ›› Issue (11) : 1745-1752 DOI: 10.7536/PC200635
review-article
Scan to read & Share
Palladium Catalyzed Heck-Type Reaction of Organic Halides and Alkyl-Alkynes
Author information +
History +
PDF

Abstract

As an important unit of molecular structure and organic building blocks, the development of new synthetic methods of allene has received much attention. The Heck and related cascade reaction of alkenes is arguably one of the most synthetically versatile method. However, the Heck reaction of alkyl-alkynes leading to allenes has lagged behind due to the energetically unfavored β-hydride elimination of vinyl palladium species. Several competitive reactions such as protonation, carbohalogenation and cascade reaction exist. Moreover, the isomerization of allene and the regioselectivity of unsymmetrical alkyl-alkynes also limited this research progress. To effectively promote β-hydride elimination of vinyl palladium species, several commonly-used strategies are the increasing reaction temperature, introduction of ortho-substituent to aryl halides and the development of ligand. In this mini-review, Heck and related reaction of alkyl-alkynes including β-hydride elimination reactions of vinyl palladium species, protonation reaction, carbohalogenation reaction, and cascade reaction are emphasized. Finally, the major limitation and an outlook this type of reaction are provided.

Contents

1 Introduction

2 Heck-type reaction pathway of alkyl-alkynes

3 Heck reaction of alkyl-alkynes

4 Other competitive reactions

4.1 Carbohalogenation process

4.2 Domino-Heck cyclization process

4.3 Activation process of aryl C-H

5 β-hydride elimination reactions

6 Conclusion and outlook

Graphical abstract

Keywords

Heck reaction / alkyl-alkynes / halides / allenes / axial chirality / protonation / carbohalogenation / cascade reaction

Cite this article

Download citation ▾
Chenghao Zhu, Junliang Zhang. Palladium Catalyzed Heck-Type Reaction of Organic Halides and Alkyl-Alkynes. Progress in Chemistry, 2020, 32(11): 1745-1752 DOI:10.7536/PC200635

登录浏览全文

4963

注册一个新账户 忘记密码

References

Funding

the National Natural Science Foundation of China(21672067)

PDF (2557KB)

2871

Accesses

0

Citation

Detail

Sections
Recommended

/

〈 〉