Journal
ACS CATALYSIS
Volume 10, Issue 15, Pages 8736-8741Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c02697
Keywords
olefin isomerization; contra-thermodynamic; chain-walking; remote functionalization; retro-hydrofunctionalization; oxidative palladium reactions
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Funding
- Chevron
- National Science Foundation
- National Institutes of Health [S10OD024998]
- UC Berkeley NMR facility
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We report a newly developed, palladium-catalyzed dehydrosilylation of terminal alkylsilanes that combines with chainwalking hydrosilylation to create a one-pot isomerization of internal olefins to terminal olefins. This catalytic dehydrosilylation is one of the few examples of thermal catalytic functionalizations of unactivated alkylsilanes. The reaction involves transmetalation of an alkylsilane, beta-hydride elimination, release of the terminal olefin, and reoxidation of the palladium catalyst. A variety of linear internal olefins underwent the overall isomerization to terminal olefins in good yields and in good regioselectivities. Particularly noteworthy, isomerizations occurring over seven carbon units proceeded in yields that are comparable to those of isomerizations occurring over one carbon unit.
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