Deoxygenative CO2 conversions with triphenylborane and phenylsilane in the presence of secondary amines or nitrogen-containing aromatics

Takumi Murata; Mahoko Hiyoshi; Shinsuke Maekawa; Yuta Saiki; Manussada Ratanasak; Jun-ya Hasegawa; Tadashi Ema

doi:10.1039/D1GC04599G

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Deoxygenative CO₂ conversions with triphenylborane and phenylsilane in the presence of secondary amines or nitrogen-containing aromatics†

Takumi Murata,^a Mahoko Hiyoshi,^a Shinsuke Maekawa,^a Yuta Saiki,^a Manussada Ratanasak,^b Jun-ya Hasegawa

^b and Tadashi Ema

*^a

Author affiliations

* Corresponding authors

^a Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan
E-mail: ema@cc.okayama-u.ac.jp

^b Institute for Catalysis, Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan

Abstract

BPh₃ catalyzed the N-methylation of secondary amines and the C-methylenation (methylene-bridge formation between aromatic rings) of N,N-dimethylanilines or 1-methylindoles in the presence of CO₂ (1 atm) and PhSiH₃ without solvent at 30–40 °C. A cascade reaction from 1-methyl-2-oxindole to 3,3′-methylenebis(1-methylindole) via 1-methylindole also proceeded.

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Article information

DOI: https://doi.org/10.1039/D1GC04599G
Article type: Communication
Submitted: 10 Dec 2021
Accepted: 18 Feb 2022
First published: 19 Feb 2022

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Green Chem., 2022,24, 2385-2390

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Deoxygenative CO₂ conversions with triphenylborane and phenylsilane in the presence of secondary amines or nitrogen-containing aromatics

T. Murata, M. Hiyoshi, S. Maekawa, Y. Saiki, M. Ratanasak, J. Hasegawa and T. Ema, Green Chem., 2022, 24, 2385 DOI: 10.1039/D1GC04599G

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