Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 15, Pages 5471-5475Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901045g
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Funding
- Program of Promotion of Environmental Improvement to Enhance Young Researchers' Independence
- Special Coordination Funds for Promoting Science and Technology
- Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
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Air-stable and commercially available alkynophilic metal salts, such as PtCl2, PtCl4, and [RuCl2(CO)(3)](2), catalyze the cycloisomerization of 1-alkyl-2-ethynylbenzenes to produce Substituted indenes even at all ambient temperature. Electrophilically activated alkynes can be intercepted by simple benzylic C-H bonds at primary, secondary, and tertiary carbon centers. Mechanistic studies, such as labeling studies and kinetic isotope and substituent effects, indicate that the cycloisomerization proceeds through the formation of a vinylidene intermediate and turnover-limiting 1,5-shift of benzylic hydrogen.
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