Synlett 2021; 32(04): 401-405
DOI: 10.1055/s-0040-1705968
cluster
Radicals – by Young Chinese Organic Chemists

Radical-Mediated Hetaryl Functionalization of Nonactivated Alkenes through Distal ipso-Migration of O- or S-Hetaryls

Huihui Zhang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, P. R. of China   eMail: chzhu@suda.edu.cn
,
Meishan Ji
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, P. R. of China   eMail: chzhu@suda.edu.cn
,
Youhao Wei
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, P. R. of China   eMail: chzhu@suda.edu.cn
,
Haodong Chen
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, P. R. of China   eMail: chzhu@suda.edu.cn
,
Xinxin Wu
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, P. R. of China   eMail: chzhu@suda.edu.cn
,
Chen Zhu
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, P. R. of China   eMail: chzhu@suda.edu.cn
b   Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
› Institutsangaben

C.Z. is grateful for the financial support from the National Natural Science Foundation of China (21722205, 21971173) and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).


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Dedicated to Ilhyong Ryu on the occasion of his 70th birthday

Abstract

A radical-mediated hetaryl functionalization of nonactivated alkenes through distal ipso-migration of O- or S-containing hetaryls was developed. Furyl, benzofuryl, thienyl, and benzothienyl groups showed satisfactory migratory abilities. A variety of heteroatom-centered radicals, including azido, trifluoromethylsulfanyl, and silyl radicals readily trigger the migration cascade, and a new C–heteroatom and C–C bond are concomitantly constructed in the reaction. This method provides an efficient approach to the synthesis of high-valued complex O- or S-hetaryl compounds.

Supporting Information



Publikationsverlauf

Eingereicht: 15. August 2020

Angenommen nach Revision: 21. September 2020

Artikel online veröffentlicht:
30. Oktober 2020

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