Issue 89, 2019
From the journal:

Chemical Communications

Rhodium(iii)-catalyzed regioselective distal ortho C–H alkenylation of N-benzyl/furanylmethylpyrazoles directed by N-coordinating heterocycles†

Hyewon Kim, ORCID logo a   Raju S. Thombal, ORCID logo a   Hari Datta Khanal ORCID logo a  and  Yong Rok Lee ORCID logo *a  

* Corresponding authors

a School of Chemical Engineering, Yeungnam University, Gyeongsan 38541, Republic of Korea
E-mail: yrlee@yu.ac.kr
Fax: +82-53-810-4631
Tel: +82-53-810-2529

Abstract

C–H activation of challenging N-benzylpyrazoles was accomplished by employing rhodium(III) catalysis. This C–H activation reaction proceeds via a six-membered rhodacycle intermediate and enables distal regioselective alkenyl-functionalization on the aromatic ring of N-benzylpyrazoles without the formation of bis-adducts. High functional group tolerance, low catalyst loading, and superior reactivity of olefin moieties towards N-benzylpyrazoles are some of the attractive features of this protocol. This protocol offers a broad scope for the regioselective functionalization of indazoles, benzo[d][1,2,3]triazoles, and 1-(furan-3-ylmethyl)-1H-pyrazole in good yields.

Graphical abstract: Rhodium(iii)-catalyzed regioselective distal ortho C–H alkenylation of N-benzyl/furanylmethylpyrazoles directed by N-coordinating heterocycles

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Article information

DOI
https://doi.org/10.1039/C9CC06758B
Article type
Communication
Submitted
30 Aug 2019
Accepted
11 Oct 2019
First published
14 Oct 2019

Chem. Commun., 2019,55, 13402-13405

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Rhodium(III)-catalyzed regioselective distal ortho C–H alkenylation of N-benzyl/furanylmethylpyrazoles directed by N-coordinating heterocycles

H. Kim, R. S. Thombal, H. D. Khanal and Y. R. Lee, Chem. Commun., 2019, 55, 13402 DOI: 10.1039/C9CC06758B

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