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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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Published in: | Synthetic communications 2019-04, Vol.49 (7), p.942-949 |
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Main Authors: | , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0039-7911 1532-2432 |
DOI: | 10.1080/00397911.2019.1581893 |