Visible‐Light Photoredox Catalyzed Regioselective 1,4‐Hydroalkylation of 1,3‐Enyne

Abstract

Described herein is a visible‐light photoredox‐catalyzed regioselective 1,4‐hydroalkylation of 1,3‐enynes. Various of di‐ and tri‐substituent allenes were really accessible under the present reaction conditions. The visible‐light photoredox activation of the carbon nucleophile to generate its radical species, allowing the addition with un‐activated enynes. The synthetic utility for the present protocol was demonstrated by a large‐scale reaction, as well as the derivatization of the allene product.

Photoredox-Catalyzed 1,4-Peroxidation–Sulfonylation of Enynones: A Three-Component Radical Coupling Approach for the Synthesis of Highly Functionalized Allenes

“…More recently, the Wang’s group developed the dual 4-CzIPN photoredox and chromium catalysis for the asymmetric 1,4-difunctionalization of 1,3-enynes to the chiral allenols . In contrast to the previous dual metal/photoredox catalysis approaches, the Zhang’s group explored the dual Ir-photoredox/NHC-catalyzed 1,4-sulfonylacylation of 1,3-enynes using sodium sulfinate salts and aroyl fluorides . Such a nonmetal-based 1,4-hydroxysulfonylation of 1,3-enynes was also explored by the Wu’s group under the Ir-photoredox catalysis using water and sulfonyl chlorides .…”

Visible-Light-Mediated Radical Hydroalkylative Cyclization of 1,6-Enynes

“…In a continuation of our research on synthetic methodology development toward heterocyclic compound formation, we herein developed a hydroalkylative cyclization reaction using Ir­(dtbbpy)­(ppy) 2 PF 6 as the catalyst, dimethyl malonate as a carbon atom radical source, and 1,6-enyne as substrate, giving pyrrolidine and furan derivatives in good yields.…”