Magnesium-mediated sp3 C–H activation in cascade cyclization of 1-arylethynyl-2-alkyl-o-carboranes: efficient synthesis of carborane-fused cyclopentanes,Chemical Science

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Magnesium-mediated sp3 C–H activation in cascade cyclization of 1-arylethynyl-2-alkyl-o-carboranes: efficient synthesis of carborane-fused cyclopentanes
Chemical Science ( IF 7.6 ) Pub Date : 2020-09-02 , DOI: 10.1039/d0sc04465b
Jie Zhang ₁ , Cen Tang ₁ , Zuowei Xie ₁

Affiliation

This work reports an unprecedented cascade cyclization of 1-arylethynyl-2-alkyl-o-carboranes promoted by magnesium-mediated sp³ C–H activation. Treatment of 1-arylethynyl-2-alkyl-o-carboranes with MeMgBr gives a series of carborane-fused cyclopentanes in very good yields. Deuterium labelling and control experiments suggest that HMgBr, resulting in situ from the nucleophilic substitution of cage B–H bonds with Grignard reagent, initiates the reaction, in which magnesium-promoted intramolecular sp³ C–H activation serves as a key step. This work not only offers a new route for the synthesis of carborane-fused cyclopentanes, but also sheds some light on Mg-mediated C–H activation and functionalization.

中文翻译：

1-芳基乙炔基-2-烷基-邻碳硼烷级联环化中镁介导的sp3 C-H活化：有效合成碳硼烷稠合环戊烷

这项工作报告了由镁介导的 sp ³ C–H 活化促进的 1-芳基乙炔基-2-烷基-邻碳硼烷前所未有的级联环化。用 MeMgBr 处理 1-芳基乙炔基-2-烷基-邻碳硼烷，以非常好的收率得到一系列碳硼烷稠合的环戊烷。氘标记和对照实验表明，HMgBr 通过格氏试剂原位亲核取代笼 B-H 键引发反应，其中镁促进的分子内 sp ³ C-H 活化是关键步骤。这项工作不仅为碳硼烷稠合环戊烷的合成提供了一条新途径，而且还为镁介导的C-H活化和功能化提供了一些线索。

更新日期：2020-09-23

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