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Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction.

ABSTRACT: We report the synthesis of unsaturated silacycles via an intramolecular silyl-Heck reaction. Using palladium catalysis, silicon electrophiles tethered to alkenes cyclize to form 5- and 6-membered silicon heterocycles. The effects of alkene substitution and tether length on the efficiency and regioselectivity of the cyclizations are described. Finally, through the use of an intramolecular tether, the first examples of disubstituted alkenes in silyl-Heck reactions are reported.

SUBMITTER: Reid WB

PROVIDER: S-EPMC7236810 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction.

Reid William B WB McAtee Jesse R JR Watson Donald A DA

Organometallics 20190926 19

We report the synthesis of unsaturated silacycles via an intramolecular silyl-Heck reaction. Using palladium catalysis, silicon electrophiles tethered to alkenes cyclize to form 5- and 6-membered silicon heterocycles. The effects of alkene substitution and tether length on the efficiency and regioselectivity of the cyclizations are described. Finally, through the use of an intramolecular tether, the first examples of disubstituted alkenes in silyl-Heck reactions are reported. ...[more]

PMID: 32431470

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