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铑(III)催化的亚砜叶立德与醌的顺序邻位C-H氧化芳基化/环化反应合成2-羟基-二苯并[b,d]吡喃-6-酮

Rh(iii)-Catalyzed sequential ortho-C-H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones.

作者信息

Dong Yaqun, Yu Jin-Tao, Sun Song, Cheng Jiang

机构信息

School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, and Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, Changzhou University, Gehu Road 1, Changzhou, 213164, P. R. China.

出版信息

Chem Commun (Camb). 2020 Jun 18;56(49):6688-6691. doi: 10.1039/d0cc00176g.

Abstract

A rhodium(iii)-catalyzed ortho-C-H functionalization of sulfoxonium ylides followed by intramolecular annulation reactions with quinones was described, where the carbonyl in sulfoxonium ylides served as a chelation group. This protocol leads to the efficient formation of 2-hydroxy-6H-benzo[c]chromen-6-one derivatives, proceeding with the cleavage of the C(O)-S bond in sulfoxonium ylides. This protocol featured high chemo-selectivity and functional group tolerance, where sulfoxonium ylides acted as the aroyl sources.

摘要

描述了一种铑(III)催化的亚砜叶立德的邻位C-H官能化反应,随后与醌进行分子内环化反应,其中亚砜叶立德中的羰基作为螯合基团。该方法能有效形成2-羟基-6H-苯并[c]色烯-6-酮衍生物,反应过程中亚砜叶立德中的C(O)-S键发生断裂。该方法具有高化学选择性和官能团耐受性,亚砜叶立德作为芳酰基源。

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