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Synlett 2023; 34(14): 1719-1722
DOI: 10.1055/s-0042-1752656
DOI: 10.1055/s-0042-1752656
letter
A Unified Approach to Mono- and 2,3-Disubstituted N–H Indoles
We thank Samsung Electronics and Samsung Electro-Mechanics (BK-21 program, Y.G.K.) and the National Science Foundation (CHE-2203224, J.K.C.) for generous financial support.
Abstract
A unified approach to mono- and disubstituted N–H indoles is described by means of oxidative cyclization of 2-alkenyl anilines, which are prepared by cross-coupling of the corresponding o-bromoanilines. This procedure is operationally expedient and tolerant of common functional groups to allow regiospecific installation of the alkyl and aryl substituents.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1752656.
- Supporting Information
Publication History
Received: 29 January 2023
Accepted after revision: 06 March 2023
Article published online:
29 March 2023
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Recent reviews:
Recent examples:
Reviews:
For representative syntheses of indole alkaloids, see inter alia:
Prepared by the Suzuki–Miyaura coupling reaction of 2-iodoaniline and cyclohexenylboronic acid pinacol ester in 97% yield:
Similarly, other 2-alkenylaniline substrates were prepared by the Suzuki–Miyaura or Stille coupling reactions, see:
One example of the indole synthesis by the same procedure (with PIFA) was reported to afford 4b in 78% yield. Interestingly, the corresponding cyclization of 1g was reported to provide traces of 2g:
Indoles 4a and 4b were synthesized by using persulfate as oxidant in 54% and 73% yield, respectively, and the intermediacy of an amine radical cation was proposed, see:
For the intermediacy of metal nitrenoids, see: