Borane-catalyzed dehydrogenative C–C bond formation of indoles with N-tosylhydrazones: an experimental and computational study

A novel dehydrogenative C–C bond formation of indoles and N-tosylhydrazones to give di(indolyl)methanes (DIMs) has been demonstrated using tris(pentafluorophenyl)borane as a catalyst. A wide range of functional groups can be tolerated under this metal-free protocol to afford symmetrical and most imp...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-06, Vol.9 (13), p.3428-3437
Main Authors: Dipika, Sharma, Yogesh Brijwashi, Pant, Suyash, Dhaked, Devendra Kumar, Guru, Murali Mohan
Format: Article
Language:English
Subjects:
Adducts
Bonding
Boranes
Catalysts
Computer applications
Covalent bonds
Dehydrogenation
Functional groups
Indoles
Intermediates
Organic chemistry
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Summary:A novel dehydrogenative C–C bond formation of indoles and N-tosylhydrazones to give di(indolyl)methanes (DIMs) has been demonstrated using tris(pentafluorophenyl)borane as a catalyst. A wide range of functional groups can be tolerated under this metal-free protocol to afford symmetrical and most importantly unsymmetrical DIMs. Extensive experimental investigations like the kinetic profile, Hammett plot, determination of reaction order, and HRMS analysis for intermediates along with computational study suggest that the reaction proceeds through sequential intermolecular C–C/C–C bond formation with indoles and borane adducts of N-tosylhydrazones followed by acceptorless dehydrogenation for the access of bioactive DIMs.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00552b