Synlett 2022; 33(20): 2026-2032
DOI: 10.1055/a-1928-7308
letter

A Reductive Benzylation for Benzenes Using Aroyl Chlorides and Triethylsilane Catalyzed by Aluminosilicate-Stabilized Silyl Cations on Montmorillonite

Yoshiki Tanaka
a   Department of Chemistry for Life Sciences and Agriculture, Faculty of Life Sciences, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya, Tokyo 156-8502, Japan
,
Shintaro Shibata
b   Graduate School of Arts and Sciences, The University of Tokyo, 8-3-1 Komaba, Meguro, Tokyo 153-8902, Japan
,
Kimiko Hashimoto
a   Department of Chemistry for Life Sciences and Agriculture, Faculty of Life Sciences, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya, Tokyo 156-8502, Japan
,
Yoichi Masui
b   Graduate School of Arts and Sciences, The University of Tokyo, 8-3-1 Komaba, Meguro, Tokyo 153-8902, Japan
,
Makoto Onaka
a   Department of Chemistry for Life Sciences and Agriculture, Faculty of Life Sciences, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya, Tokyo 156-8502, Japan
› Author Affiliations
Financial supports from the Japan Society for the Promotion of Science (JSPS KAKENHI Grant number JP19K05157) and the White Rock Foundation are gratefully acknowledged.


Abstract

We discovered that the aluminosilicate-stabilized silyl cations, which were created from a solid-acid catalyst, the proton-exchanged montmorillonite, and Et3SiH, efficiently promoted the reductive benzylation of benzenes with aromatic carboxylic acid chlorides and Et3SiH in one pot.

Supporting Information



Publication History

Received: 22 June 2022

Accepted after revision: 22 August 2022

Accepted Manuscript online:
22 August 2022

Article published online:
11 October 2022

© 2022. Thieme. All rights reserved

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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