Palladium-Catalyzed Hydrofunctionalization of Vinyl Phenol Derivatives with Heteroaromatics

Abstract

A hydroheteroarylation reaction of vinyl phenols using an alkyl chloride as the sacrificial hydride source is reported. The method tolerates a wide range of heterocycles as the exogenous nucleophile including indoles and pyrroles. The resulting products are easily processed to biologically relevant scaffolds.

Redox‐Neutral α,β‐Difunctionalization of Cyclic Amines

“…Interestingly, the main product of this reaction was the unusual N,O-acetal 7 a, which was isolated as a single diastereomer in 78 % yield [11] (relative configuration established by X-ray crystallography). [12][13][14][15] The formation of product 7 a is consistent with the intermediacy of an endocyclic enamine, corresponding to proposed compound 6 (Scheme 1). Considering that the formation of 7 a from 2 a requires the incorporation of one unit of benzaldehyde (or a benzaldehyde equivalent), we performed the reactions outlined in Equation (2).…”

Applications of ortho-Quinone Methide Intermediates in Catalysis and Asymmetric Synthesis

“…29 The scope of this transformation is found to be broad in both reaction partners (Figure 10). Here, oxidative addition of the alkyl chloride to Pd 0 results in Pd-alkyl intermediate A .…”

Pd‐Catalyzed Hydrogen‐Transfer Reactions from Alcohols to C=C, C=O, and C=N Bonds

“…Having observed the particular reactivity of 2‐alkenylphenols (see below, Section 2.1.2.d), Sigman's team carried out the reaction between 2‐vinylphenol and N ‐methylindole by their procedure [Equation (16)] 37. The modest yield led the authors to look for a better sacrificial hydride source.…”

“…The modest yield led the authors to look for a better sacrificial hydride source. They finally obtained improved results with n BuCl in place of 1‐phenylethanol 37 …”