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. 2022 May 3;12(21):13314-13318.
doi: 10.1039/d2ra02127g. eCollection 2022 Apr 28.

Highly selective cross-coupling reactions of 1,1-dibromoethylenes with alkynylaluminums for the synthesis of aryl substituted conjugated enediynes and unsymmetrical 1,3-diynes

Kun Wu  1 , Chuan Wu  1 , Xiao-Ying Jia  1 , Lin Zhou  1 , Qing-Han Li  1
Affiliations

Highly selective cross-coupling reactions of 1,1-dibromoethylenes with alkynylaluminums for the synthesis of aryl substituted conjugated enediynes and unsymmetrical 1,3-diynes

Kun Wu et al. RSC Adv. .

Abstract

A highly efficient method for the synthesis of aryl substituted conjugated enediynes and unsymmetrical 1,3-diynes via selective cross-coupling reactions of 1,1-dibromoethylenes with alkynylaluminums using the Pd(OAc)2-DPPE and Pd2(dba)3-TFP complexes as catalysts, respectively, has been successfully developed. Though the alkyl substituted conjugated enediynes and unsymmetrical 1,3-diynes were not obtained, this case is also remarkable as the same starting materials could selectively produce either aryl substituted conjugated enediynes or unsymmetrical 1,3-diynes in moderate to excellent yields (up to 99%) in the different Pd-phosphine catalytic systems.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. The coupling reactions involving 1,1-dibromoethylenes 1 (a–d).
Scheme 2
Scheme 2. Proposed catalytic cycles.
See this image and copyright information in PMC

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