Lewis base-promoted carboncarbon sp3sp3 coupling reactions of -silyl silylethersElectronic supplementary information (ESI) available: Experimental procedulres and spectroscopic data for all new compounds. See DOI: 10.1039/c2sc00581f

A Lewis base-promoted addition of -silyl silylethers to primary halides has been developed. This new carboncarbon sp 3 sp 3 bond-forming process accesses an unconventional reactivity pattern (d 1 synthon) from easily accessible precursors. The strategy accommodates a variety of primary alkyl, allyli...

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Bibliographic Details
Main Authors Brekan, Jonathan A, Chernyak, Dmitri, White, Kolby L, Scheidt, Karl A
Format Journal Article
LanguageEnglish
Published 05.03.2012
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Summary:A Lewis base-promoted addition of -silyl silylethers to primary halides has been developed. This new carboncarbon sp 3 sp 3 bond-forming process accesses an unconventional reactivity pattern (d 1 synthon) from easily accessible precursors. The strategy accommodates a variety of primary alkyl, allylic and benzylic electrophiles and -silyl silylethers. These d 1 synthons have also been used in the synthesis of cross pinacol and benzil products. Mechanistic studies indicate significant intermolecular silyl group exchange during the reaction. An Umpolung d1 synthon-type reaction using -silyl silylethers and fluoride as the Lewis base has been developed.
Bibliography:10.1039/c2sc00581f
Electronic supplementary information (ESI) available: Experimental procedulres and spectroscopic data for all new compounds. See DOI
ISSN:2041-6520
2041-6539
DOI:10.1039/c2sc00581f