A domino palladium-catalyzed C-C and C-O bonds formation via dual O-H bond activation: Synthesis of 6,6-dialkyl-6 H -benzo[ c ]chromenes

Mahendar, L and Krishna, J and Gopi Krishna Reddy, A and B, Venkat Ramulu and G, Satyanarayana (2012) A domino palladium-catalyzed C-C and C-O bonds formation via dual O-H bond activation: Synthesis of 6,6-dialkyl-6 H -benzo[ c ]chromenes. Organic Letters, 14 (2). pp. 628-631. ISSN 1523-7060

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Abstract

An efficient Pd-catalyzed domino reaction of α,α-dialkyl-(2- bromoaryl)methanols to 6,6-dialkyl-6H-benzo[c]chromenes is presented. Their formation can be explained via a five membered Pd(II)-cycle that efficiently involves a domino homocoupling with the second molecule, β-carbon cleavage, and finally intramolecular Buchwald-Hartwig cyclization. This domino process effectively involves breaking of five σ-bonds (2C-Br, 2O-H, and a C-C) and formation of two new σ-bonds (C-C and C-O). This mechanistic pathway is unprecedented and further illustrates the power of transition metal catalysis

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IITH Creators:
IITH CreatorsORCiD
G, SatyanarayanaUNSPECIFIED
Item Type: Article
Subjects: ?? sub5.8 ??
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 17 Nov 2014 06:00
Last Modified: 31 Dec 2015 11:08
URI: http://raiith.iith.ac.in/id/eprint/827
Publisher URL: http://dx.doi.org/10.1021/ol2032625
OA policy: http://www.sherpa.ac.uk/romeo/issn/1523-7060/
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