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Synthesis of 1-aryl- benzocycloalkane derivatives via one-pot two-step reaction of benzocyclonone, tosylhydrazide, and arylboronic acid

A metal-free one-pot two-step reductive coupling reaction of benzocyclonone, tosylhydrazide, and arylboronic acid was developed for the formation of a C(sp 3 )-C(sp 2 ) bond, which enabled the efficient synthesis of 1-aryl-benzocycloalkane compounds in moderate to good yields on a multi-gram scale....

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Bibliographic Details
Published in:Synthetic communications 2019-04, Vol.49 (7), p.942-949
Main Authors: Liu, Shijuan, Fang, Meitong, Yin, Dongni, Wang, Yanan, Liu, Lei, Li, Xiuying, Che, Guangbo
Format: Article
Language:English
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Summary:A metal-free one-pot two-step reductive coupling reaction of benzocyclonone, tosylhydrazide, and arylboronic acid was developed for the formation of a C(sp 3 )-C(sp 2 ) bond, which enabled the efficient synthesis of 1-aryl-benzocycloalkane compounds in moderate to good yields on a multi-gram scale. Moreover, five- and six-membered benzocyclic ketones are also suitable substrates for this reaction. Notably, this protocol was also found to be suitable for synthesizing 3-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-one, an important intermediate in the synthesis of indatraline.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2019.1581893