Loading…

Photocatalytic Chemodivergent Synthesis of α‐gem‐Dihalovinyl Ketones and Chromen‐2‐Ones from Monoalkynes

A general photocatalytic substrate‐controlled chemodivergent strategy starting from monoalkynes with polyhalomethanes such as BrCCl3 and CBr4 was develop, enabling Kharasch‐type addition/nucleophilic substitution cascade to selectively produce α‐gem‐dihalovinyl ketones and chromen‐2‐ones with modera...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-08, Vol.364 (15), p.2666-2672
Main Authors: Xu, Zi‐Yang, Liu, Yin‐Ping, Liu, Xin, Fu, Rong, Hao, Wen‐Juan, Tu, Shu‐Jiang, Jiang, Bo
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A general photocatalytic substrate‐controlled chemodivergent strategy starting from monoalkynes with polyhalomethanes such as BrCCl3 and CBr4 was develop, enabling Kharasch‐type addition/nucleophilic substitution cascade to selectively produce α‐gem‐dihalovinyl ketones and chromen‐2‐ones with moderate to good yields. Use of monoalkynes without additional nucleophilic sites furnished α‐gem‐dihalovinyl ketones through a Kharasch‐type addition and intermolecular allylic substitution cascade whereas the latter transformation of 2‐ethynylphenols allowed the full breaking of carbon‐halogen bonds of BrCX3 to access functionalized chromen‐2‐ones. The late‐stage application of these resulting α‐gem‐dihalovinyl ketones demonstrates the versatility of their derivatization.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200422