Journal
ORGANIC LETTERS
Volume 20, Issue 12, Pages 3596-3600Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01382
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Funding
- NSFC [21472071, 21602087]
- PAPD of Jiangsu Higher Education Institutions
- Outstanding Youth Fund of JSNU [YQ2015003]
- NSF of Jiangsu Province [BK20160212]
- Qing Lan Project of Jiangsu Education Committee
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A new combination of anti-Baldwin 3-exo-dig cyclization with 1,2-alkynyl migration of 1,4-enynes with simple cycloalkanes was established, enabling C-C breaking and reconstruction to access a wide range of alpha-alkynyl ketones with generally good yields by FeCl2/ditert-butyl peroxide (DTBP) as a catalytic oxidation system. Radical induced C(sp(3))-H functionalization of cycloalkanes was realized, leading to the direct formation of C(sp(3))-C(sp(3)) and C(sp)-C(sp(3)) bonds. The mechanism for forming alpha-alkynyl ketones was proposed.
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