Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates

Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates

April 2024 Vol.67 No.4: 1175–1180 | Hao-Dong Qian, Xiang Li, Tingrui Yin, Wei-Feng Qian, Chunhui Zhao, Cuiju Zhu & Hao Xu
The article describes a novel strategy for the copper-catalyzed asymmetric heteroarylation of yne-thiophene carbonates using indoles via remote substitution. The key innovation lies in the design of an alkynyl group at the ortho-position of the thiophene heterocycle, enabling the formation of a triarylmethane moiety through very remote substitution. This approach extends the concept of remote copper-catalyzed asymmetric transformations to yne-aryl esters, providing a versatile method for synthesizing chiral triarylmethanes with high efficiency, enantioselectivity, and excellent functional group compatibility. The reaction is also amenable to follow-up transformations, making it useful for the synthesis of various enantioenriched building blocks. Preliminary mechanistic studies support the plausibility of the remote substitution pathway. The study highlights the potential of this method in expanding the application of copper-catalyzed remote substitutions.The article describes a novel strategy for the copper-catalyzed asymmetric heteroarylation of yne-thiophene carbonates using indoles via remote substitution. The key innovation lies in the design of an alkynyl group at the ortho-position of the thiophene heterocycle, enabling the formation of a triarylmethane moiety through very remote substitution. This approach extends the concept of remote copper-catalyzed asymmetric transformations to yne-aryl esters, providing a versatile method for synthesizing chiral triarylmethanes with high efficiency, enantioselectivity, and excellent functional group compatibility. The reaction is also amenable to follow-up transformations, making it useful for the synthesis of various enantioenriched building blocks. Preliminary mechanistic studies support the plausibility of the remote substitution pathway. The study highlights the potential of this method in expanding the application of copper-catalyzed remote substitutions.
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