Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 6, Pages 4714-4732Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00104
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Funding
- Natural Science Foundation of Guangdong Province [2018A030310680]
- Research Foundation of Department of Education of Guangdong Province [2018KTSCX236, 2020KTSCX154]
- Science Foundation for Young Teachers of Wuyi University [2019td09]
- College Students Innovation and Entrepreneurship Training Program of Wuyi University [2020CX08]
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An unprecedented copper-catalyzed tandem reaction of 1,6-enynes with diazo compounds via a cross-coupling/[2 + 2] cycloaddition sequence was reported, leading to the synthesis of a library of methylenecyclobutane-fused ring systems with high proximal-regioselectivity and diastereoselectivity. Moreover, the key intermediate of 1,6-allenene proceeds via a thermally promoted [2 + 2] cycloaddition in the absence of copper catalyst.
An unprecedented copper-catalyzed tandem reaction of 1,6-enynes with diazo compounds via a cross-coupling/[2 + 2] cycloaddition sequence was reported. A library of methylenecyclobutane-fused ring systems including cyclobuta[b]indolines, cyclobuta[b]benzofuran, benzo[b]cyclobuta[d]thiophene, and bicyclo[3.2.0] structures were obtained in moderate to excellent yields under very mild reaction conditions. The reaction exhibited high proximal-regioselectivity and diastereoselectivity. Moreover, 1,6-allenene has proven to be the key intermediate and proceeds via a thermally promoted [2 + 2] cycloaddition in the absence of copper catalyst.
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