Synthesis of unsymmetrical diarylmethanols via C–Si bond bifunctionalization enabled by sequential [1,4]-Csp2 to O-silyl migration

Tianbao Hu; Liying Huang; Lu Gao; Zhenlei Song

doi:10.1039/C9QO01450K

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Synthesis of unsymmetrical diarylmethanols via C–Si bond bifunctionalization enabled by sequential [1,4]-Csp² to O-silyl migration†

Tianbao Hu,^a Liying Huang,^a Lu Gao*^a and Zhenlei Song

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
E-mail: lugao@scu.edu.cn, zhenleisong@scu.edu.cn

Abstract

Unsymmetrical C–Si bond bifunctionalization of 2,2′-bis(trimethylsilyl) diphenylmethanol has been developed via an “on–off–on” sequential [1,4]-Csp² to O-silyl migration. The approach enables installing Csp³/Csp³, Csp³/Csp² or Csp²/Csp³ electrophiles in one pot, leading to sterically congested unsymmetrical diarylmethanols in good yields.

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Article information

DOI: https://doi.org/10.1039/C9QO01450K
Article type: Research Article
Submitted: 05 Dec 2019
Accepted: 12 Dec 2019
First published: 19 Dec 2019

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Org. Chem. Front., 2020,7, 543-547

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Synthesis of unsymmetrical diarylmethanols via C–Si bond bifunctionalization enabled by sequential [1,4]-Csp² to O-silyl migration

T. Hu, L. Huang, L. Gao and Z. Song, Org. Chem. Front., 2020, 7, 543 DOI: 10.1039/C9QO01450K

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