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Palladium-Catalyzed Oxidative Allylic C-H Silylation.
2011 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 13, no 7, p. 1888-1891Article in journal (Refereed) Published
Abstract [en]

Pd-catalyzed allylic C-H silylation was performed using hexamethyldisilane as the silyl source. These C-H functionalization reactions occur only in the presence of hypervalent iodine reagents or other strong oxidants and proceed with excellent regioselectivity, providing the linear allylic isomer of the allylsilane products. In demonstrating the first oxidative allylic C-H silylation of alkenes, this study marks an important advance for the catalytic C-H functionalization method. E.g., reaction of CH2:CHCH2CO2CH2Ph with hexamethyldisilane in DME in the presence of 5 mol% Pd(OAc)2 and 2 equiv. of benzoyl peroxide and 4-nitrobenzoic acid as oxidants gave a 77% yield of Me3SiCH2CH:CHCO2CH2Ph. [on SciFinder(R)]

Place, publisher, year, edition, pages
American Chemical Society , 2011. Vol. 13, no 7, p. 1888-1891
Keywords [en]
palladium catalyzed oxidative allylic carbon hydrogen bond silylation hexamethyldisilane, allylic silane regioselective prepn
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-374753DOI: 10.1021/ol200445bOAI: oai:DiVA.org:uu-374753DiVA, id: diva2:1282029
Note

Copyright (C) 2019 American Chemical Society (ACS). All Rights Reserved.; CAPLUS AN 2011:298043(Journal; Online Computer File)

Available from: 2019-01-23 Created: 2019-01-23 Last updated: 2019-01-23

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