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Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst.

ABSTRACT: Recently we reported a second-generation ligand, bis(3,5-di-tert-butylphenyl)(tert-butyl)phosphine, for the preparation of allyl silanes using the silyl-Heck reaction. We now show that this new ligand also provides superior reactivity in the preparation of vinylsilanes from styrene derivatives. For the first time, this new ligand provides exceptionally high yields of trialkylvinylsilanes using a widely available palladium pre-catalyst, Pd2(dba)3. Finally, we demonstrate that this new catalyst system is able to form more highly decorated all carbon substituted vinylsilanes that have been shown to possess superior reactivity in oxidation and cross coupling reactions.

SUBMITTER: McAtee JR

PROVIDER: S-EPMC4912221 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst.

McAtee Jesse R JR Krause Sarah B SB Watson Donald A DA

Advanced synthesis & catalysis 20150714 10

Recently we reported a second-generation ligand, bis(3,5-di-tert-butylphenyl)(tert-butyl)phosphine, for the preparation of allyl silanes using the silyl-Heck reaction. We now show that this new ligand also provides superior reactivity in the preparation of vinylsilanes from styrene derivatives. For the first time, this new ligand provides exceptionally high yields of trialkylvinylsilanes using a widely available palladium pre-catalyst, Pd2(dba)3. Finally, we d ...[more]

PMID: 27325912

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