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Photoinduced Merging with Copper‐ or <scp>Nickel‐Catalyzed</scp> 1,<scp>4‐Cyanoalkylarylation</scp> of 1,<scp>3‐Enynes</scp> to Access Multiple Functionalizatized Allenes in Batch and Continuous Flow

2022/03/31 by Qi Sun, Xin‐Peng Zhang, Xiu Duan +7
Chemistry · #Catalytic C–H Functionalization Methods #Radical Photochemical Reactions #Sulfur-Based Synthesis Techniques

paper · doi:10.1002/cjoc.202200056

openalex publication_date 2022/03/31 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/30

Abstract

Comprehensive Summary A three‐component reaction of 1,3‐enynes and cyclobutanone oxime esters in the presence of aryl boronic acids or organozinc reagents via the photoredox/copper or photoredox/nickel catalysis has been established. This redox‐neutral 1,4‐cyanoalkylarylation reaction has demonstrated mild condition, high catalytic reactivity and wide functional group compatibility, allowing access to a variety of functionalized tetra‐substituted allene derivatives with high chemo‐ and regioselectivity. Moreover, using photocatalytic continuous flow technique to promote this process would result in increased yields (70% in flow vs. 61% in batch), reduced reaction times (7 min in flow vs. 6 h in batch), and easy scale‐up (upgrade to gram scale), showcasing its potential as a synthetic platform.

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