Manganese(III) Triacetate-Mediated Cross Coupling of Organoboron Compounds with Trichloroethylene (TCE): Synthesis of 1,1-Dichloroalkenes

Herein, we report an efficient method for the synthesis of 1,1-dichloroalkenes from organoboron compounds. This reaction proceeds in the presence of manganese(III) triacetate using trichloroethylene (TCE) as the vinylation reagent. This reaction can tolerate various types of organoboron compounds and various functional groups. The yields are moderate to good. Surprisingly, this transformation could even be achieved in the presence of manganese(II) acetate. Furthermore, this synthetic strategy could be applied to the synthesis of 1,1,2-trichloro-, 1-chloro-, and 2-chloroalkenes.

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Journal
The Journal of Organic Chemistry
Published
2024-09-17
DOI
https://doi.org/10.1021/acs.joc.4c00635
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Manganese(III) Triacetate-Mediated Cross Coupling of Organoboron Compounds with Trichloroethylene (TCE): Synthesis of 1,1-Dichloroalkenes

Xiaowei Liu, Huan Li, Zhiyuan Xu
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Manganese(III) Triacetate-Mediated Cross Coupling of Organoboron Compounds with Trichloroethylene (TCE): Synthesis of 1,1-Dichloroalkenes

Xiaowei Liu, Huan Li, Zhiyuan Xu
article en

Abstract

Herein, we report an efficient method for the synthesis of 1,1-dichloroalkenes from organoboron compounds. This reaction proceeds in the presence of manganese(III) triacetate using trichloroethylene (TCE) as the vinylation reagent. This reaction can tolerate various types of organoboron compounds and various functional groups. The yields are moderate to good. Surprisingly, this transformation could even be achieved in the presence of manganese(II) acetate. Furthermore, this synthetic strategy could be applied to the synthesis of 1,1,2-trichloro-, 1-chloro-, and 2-chloroalkenes.

The Journal of Organic ChemistryVol. 89(19)
Wenzhou University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 89%
Catalytic C–H Functionalization Methods
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