Journal
NATURE COMMUNICATIONS
Volume 11, Issue 1, Pages -Publisher
NATURE RESEARCH
DOI: 10.1038/s41467-020-20182-4
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Funding
- National Institutes of Health [5R35GM125052-03, 1R35GM128779]
- Pfizer, Inc.
- Alfred P. Sloan Fellowship Program
- Camille Dreyfus Teacher-Scholar Program
- Cottrell Scholars Program
- NSF
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2,3-Dihydrobenzofurans and indolines are common substructures in medicines and natural products. Herein, we describe a method that enables direct access to these core structures from non-conjugated alkenyl amides and ortho-iodoanilines/phenols. Under palladium(II) catalysis this [3+2] heteroannulation proceeds in an anti-selective fashion and tolerates a wide variety of functional groups. N-Acetyl, -tosyl, and -alkyl substituted ortho-iodoanilines, as well as free -NH2 variants, are all effective. Preliminary results with carbon-based coupling partners also demonstrate the viability of forming indane core structures using this approach. Experimental and computational studies on reactions with phenols support a mechanism involving turnover-limiting, endergonic directed oxypalladation, followed by intramolecular oxidative addition and reductive elimination. Dihydrobenzofurans and indolines are common substructures in medicines and natural products. Herein, the authors report a palladium-catalyzed [3+2] (hetero)annulation proceeding in an anti-selective fashion and enabling direct access to these valuable heterocycles with broad reaction scope.
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