Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 27, Pages 9280-9282Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1035557
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Funding
- National Science Foundation [CHE-0548081]
- National Institutes of Health, KU Chemical Methodologies, and Library Development Center of Excellence [P50 GM069663]
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Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.
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