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

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.

journal_name

Nat Commun

journal_title

Nature communications

authors

Ni HQ,Kevlishvili I,Bedekar PG,Barber JS,Yang S,Tran-Dubé M,Romine AM,Lu HX,McAlpine IJ,Liu P,Engle KM

doi

10.1038/s41467-020-20182-4

subject

Has Abstract

pub_date

2020-12-22 00:00:00

pages

6432

issue

1

issn

2041-1723

pii

10.1038/s41467-020-20182-4

journal_volume

11

pub_type

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