Journal
ACS CATALYSIS
Volume 6, Issue 9, Pages 6146-6150Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b01946
Keywords
dehydrogenative coupling; aerobic CuCl2 catalysis; multicomponent reaction; C-H functionalization; indole; enol
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Funding
- Natural Science Foundation of China [21332003]
- Science and Technology Commission of Shanghai Municipality [15ZR1410500]
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A sequential Rh-2(OAc)4-catalyzed multicomponent reaction and CuCl2-catalyzed postcyclization process is developed to build polyfunctional cyclopenta[b]indoles in good yields with high diastereoselectivities in an atom- and step-economic fashion. The key discovery in this process is the CuCl2-catalyzed intramolecular aerobic dehydrogenative Csp(2)-Csp(2) cross-coupling of indole C2 with an enol functionality. Mechanistic studies including X-ray photoelectron spectroscopy analysis suggest that the catalytic cycle involves Cu(II) and Cu(I). This coupling reaction represents a unique example of aerobic Cu-catalyzed direct coupling of indoles with enols under mild conditions.
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