Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 10, Pages 5639-5649Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00638
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Funding
- JSPS KAKENHI Grant [JP16H01037, JP 17H06092, JP17K17720]
- JST (ACT-C)
- Nagase Science Technology Foundation
- Yamada Science Foundation
- JST CREST [JPMJCR1522]
- Grants-in-Aid for Scientific Research [16H01037] Funding Source: KAKEN
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The rhodium(III)-catalyzed direct alkenylation of N-phenylindole-3-carboxylic acids with alkenes including acrylate ester, acrylamide, and acrylonitrile proceeds smoothly at the C4-position through regioselective C-H bond cleavage directed by the carboxyl group. In marked contrast, the indole substrates react with diarylacetylenes accompanied by cleavage of the C2-H and C2'-H bonds and decarboxylation to produce 5,6-diarylindolo [1,2-alpha] quinolone derivatives. DFT calculations have suggested that the smooth insertion of an alkene to a C4-rhodated six-membered metallacycle intermediate leads to the C4 alkenylated products, while the latter annulation at the C2- and C2'-positions is attributable to facile reductive elimination in the corresponding seven-membered metallacycles formed by the double C-H bond cleavage and alkyne insertion.
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