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- Title
Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation.
- Authors
Ni, Hui-Qi; Kevlishvili, Ilia; Bedekar, Pranali G.; Barber, Joyann S.; Yang, Shouliang; Tran-Dubé, Michelle; Romine, Andrew M.; Lu, Hou-Xiang; McAlpine, Indrawan J.; Liu, Peng; Engle, Keary M.
- Abstract
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.
- Subjects
ANNULATION; OXIDATIVE addition; NATURAL products; AMIDES; FUNCTIONAL groups; INDOLINE
- Publication
Nature Communications, 2020, Vol 11, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-020-20182-4