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Synthesis 2021; 53(13): 2229-2239
DOI: 10.1055/s-0037-1610765
paper

Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization

Wenjie Zhang
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
,
Xueyan Liu
b   Bengbu Product Quality and Inspection Institute, Bengbu, Anhui 233040, P. R. of China
,
Zhenfeng Tian
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
,
Hongji Li∗
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
› Author AffiliationsThis work was financially supported by the National Natural Science Foundation of China (21772061) and the Excellent Young Talents Fund Program of Higher Education Institutionsof Anhui Province (gxyq2020015).
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Abstract

We herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

Key words

rhodium catalysis - nitrosoanilines - azoxybenzenes - olefination - alkylation

Supporting Information



Publication History

Received: 20 November 2020

Accepted after revision: 27 January 2021

Article published online:
15 February 2021

© 2021. Thieme. All rights reserved

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