Issue 85, 2021
From the journal:

Chemical Communications

Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy†

Chaolumen Bai,a   Bao Chao,a   Tegshi Muschin,a   Agula Bao,a   Menghe Baiyin, ORCID logo a   Dan Liua  and  Yong-Sheng Bao ORCID logo *a  

* Corresponding authors

a College of Chemistry and Environmental Science, Inner Mongolia Key Laboratory of Green Catalysis, Inner Mongolia Normal University, Hohhot, China
E-mail: sbbys197812@163.com
Tel: +86-471-4392442

Abstract

The regiodivergent catalytic dehydrogenative cross-coupling reactions at both sp2 and sp3 hybridized carbons of aromatic compounds are particularly challenging. Herein, we report the finding of transient directing group controlled regiodivergent C(sp3)–C(sp2) and C(sp2)–C(sp2) cross-coupling in the o-methyl benzaldehyde frameworks. Catalyzed by palladium, using K2S2O8 or [F+] reagents as by-standing oxidants and unactivated arenes as substrates/solvents, various benzyl benzaldehydes or phenyl benzaldehydes were prepared. A mechanism study indicated that the regiospecificity is dominated by the [5,6]-fused palladacycle or [6,5]-fused palladacycle intermediates, which are generated from Pd-chelation with specified transient directing groups and further C–H activations.

Graphical abstract: Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy

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Article information

DOI
https://doi.org/10.1039/D1CC04121E
Article type
Communication
Submitted
29 Jul 2021
Accepted
29 Sep 2021
First published
29 Sep 2021

Chem. Commun., 2021,57, 11229-11232

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Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy

C. Bai, B. Chao, T. Muschin, A. Bao, M. Baiyin, D. Liu and Y. Bao, Chem. Commun., 2021, 57, 11229 DOI: 10.1039/D1CC04121E

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