Reductive Arene Ortho-silanolization of Aromatic Esters with Hydridosilyl Acetals

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2015 Feb 4

PMID 25646601

Citations 3

Authors

Yuanda Hua

Parham Asgari

Udaya Sree Dakarapu

Junha Jeon

Affiliations

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Abstract

This work describes the design and application of a single-pot, reductive arene C-H silanolization of aromatic esters for synthesis of ortho-formyl arylsilanols. This strategy involves a sequence of two transition metal (Ir and Rh)-catalyzed reactions for reductive arene ortho-silylation directed by hydridosilyl acetals and hydrolysis.

Citing Articles

Catalytic Net Oxidative C-C Activation and Silylation of Cyclopropanols with a Traceless Acetal Directing Group.

Avullala T, Nguyen H, Dakarapu U, Asgari P, Hua Y, Jeon J ACS Catal. 2022; 12(3):1764-1774.

PMID: 35573128 PMC: 9097959. DOI: 10.1021/acscatal.1c04628.

Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive -C-H silylation of phenols with traceless acetal directing groups.

Asgari P, Dakarapu U, Nguyen H, Jeon J Tetrahedron. 2017; 73(29):4052-4061.

PMID: 28694551 PMC: 5501486. DOI: 10.1016/j.tet.2016.12.002.

Catalytic Reductive ortho-C-H Silylation of Phenols with Traceless, Versatile Acetal Directing Groups and Synthetic Applications of Dioxasilines.

Hua Y, Asgari P, Avullala T, Jeon J J Am Chem Soc. 2016; 138(25):7982-91.

PMID: 27265033 PMC: 5103641. DOI: 10.1021/jacs.6b04018.