Issue 8, 2021
From the journal:

Chemical Science

o-Quinone methide with overcrowded olefin component as a dehydridation catalyst under aerobic photoirradiation conditions†

Daisuke Uraguchi, ORCID logo a   Kohsuke Kato ORCID logo b  and  Takashi Ooi ORCID logo *b  

* Corresponding authors

a Institute for Catalysis, Hokkaido University, Sapporo 001-0021, Japan

b Institute of Transformative Bio-Molecules (WPI-ITbM), Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, Japan
E-mail: tooi@chembio.ngoya-u.ac.jp

Abstract

An o-quinone methide (o-QM) featuring an overcrowded olefinic framework is introduced, which exhibits dehydridation activity owing to its enhanced zwitterionic character, particularly through photoexcitation. The characteristics of this o-QM enable the operation of dehydridative catalysis in the oxidation of benzylic secondary alcohols under aerobic photoirradiation conditions. An experimental analysis and density functional theory calculations provide mechanistic insights; the ground-state zwitterionic intermediate abstracts a hydride and proton simultaneously, and the active oxygen species facilitate catalyst regeneration.

Graphical abstract: o-Quinone methide with overcrowded olefin component as a dehydridation catalyst under aerobic photoirradiation conditions

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Article information

DOI
https://doi.org/10.1039/D0SC06240E
Article type
Edge Article
Submitted
12 Nov 2020
Accepted
10 Jan 2021
First published
15 Jan 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 2778-2783

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o-Quinone methide with overcrowded olefin component as a dehydridation catalyst under aerobic photoirradiation conditions

D. Uraguchi, K. Kato and T. Ooi, Chem. Sci., 2021, 12, 2778 DOI: 10.1039/D0SC06240E

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