Synthesis of 2‐Benzyl‐3,4‐dihydronaphthalenes via Oxidative Radical Opening/Cyclization of Methylenecyclopropanes with Potassium Benzyltrifluoroborates

A Copper‐catalyzed benzylation of methylenecyclopropanes with potassium benzyltrifluoroborate salts has been developed to produce 2‐benzyl‐3,4‐dihydronaphthalenes in moderate to good yields. This oxidative cyclization reaction proceeds well via a sequence of radical addition, ring‐opening, and cycli...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-01, Vol.2022 (2), p.n/a
Main Authors: Nie, Yu, Cheng, Li, Chen, Lihui, Li, Zhongxian, Leng, Yuting, Wu, Junliang
Format: Article
Language:English
Subjects:
Alkylation
Cyclization
Methylenecyclopropanes
Potassium
Radical reactions
Ring expansion
Substrates
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Summary:A Copper‐catalyzed benzylation of methylenecyclopropanes with potassium benzyltrifluoroborate salts has been developed to produce 2‐benzyl‐3,4‐dihydronaphthalenes in moderate to good yields. This oxidative cyclization reaction proceeds well via a sequence of radical addition, ring‐opening, and cyclization. This protocol represents a new example of methylenecyclopropane oxidative cyclization and tolerates a diverse range of substrate. Here reports a copper‐catalyzed approach for the synthesis of 2‐benzyl‐3,4‐dihydronaphthalenes. The reaction was proposed to proceed by a sequence of radical addition, ring‐opening, and cyclization of methylenecyclopropanes with potassium benzyltrifluoroborate. Such a method features operational simplicity, mild reaction conditions and widely functional group tolerance and accords a diverse array of 3,4‐dihydronaphthalenes in moderate to good yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101406