Journal
ORGANIC LETTERS
Volume 18, Issue 7, Pages 1534-1537Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00244
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Funding
- CSIR, New Delhi
- NIPER
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An oxidative dearomatization chemistry of 2-arylindole via a unique pathway involving Pd-catalyzed C-H peroxygenation is documented. Coupled with cascade transformation, it provides a new route to access indolin-3-ones bearing a C2-quaternary functionality, including a chiral center (indoxyls), a motif prevalent in indole alkaloids but synthetically underexplored. The method is chemo- and regioselective and compatible with versatile substrates. A mechanism has been outlined on the basis of results of control experiments, isolation/use of intermediates, and spectroscopic studies.
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