Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation

Hui-Qi Ni, Ilia Kevlishvili, Pranali G. Bedekar, Joyann S. Barber, Shouliang Yang, Michelle Tran-Dubé, Andrew M. Romine, Hou-Xiang Lu, Indrawan J. McAlpine (), Peng Liu () and Keary M. Engle ()
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Hui-Qi Ni: The Scripps Research Institute
Ilia Kevlishvili: University of Pittsburgh
Pranali G. Bedekar: The Scripps Research Institute
Joyann S. Barber: Pfizer Oncology Medicinal Chemistry
Shouliang Yang: Pfizer Oncology Medicinal Chemistry
Michelle Tran-Dubé: Pfizer Oncology Medicinal Chemistry
Andrew M. Romine: The Scripps Research Institute
Hou-Xiang Lu: The Scripps Research Institute
Indrawan J. McAlpine: Pfizer Oncology Medicinal Chemistry
Peng Liu: University of Pittsburgh
Keary M. Engle: The Scripps Research Institute

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-20182-4

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