Journal
ORGANIC LETTERS
Volume 21, Issue 11, Pages 4322-4326Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01492
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Funding
- Guangdong Innovative and Entrepreneurial Research Team Program [2016ZT06Y337]
- National Science AMP
- Technology Major Project Key New Drug Creation and Manufacturing Program China [2018ZX09711002-006]
- China Postdoctoral Science Foundation [2018M633258]
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An efficient and novel rhodium-catalyzed formal C-O insertion reaction of alkyne-tethered diazo compounds for the synthesis of 3H-indol-3-ols is described. A type of donor/donor rhodium carbene generated in situ via a carbene/alkyne metathesis (CAM) process is the key intermediate and terminates in a unique transformation different from donor/acceptor carbenoids. In addition, O-18-labeling experiments indicate that intramolecular oxygen-atom transfer from the amide group to the carbon-carbon triple bond occurs during this transformation.
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