Palladium-Catalyzed Synthesis of β-Alkynyl Ketones via Selective 1,3-Alkynyl Migration of α,α-Disubstituted Allylic Alcohols

Herein, a palladium-catalyzed 1,3-alkynyl migration of allylic alcohol for the synthesis of β-alkynyl ketone was described. This intramolecular rearrangement reaction demonstrated an enhanced reactivity compared to the traditional intermolecular alkynylation by circumventing the dimerization of alkynes, exhibiting a specific selectivity toward β-alkynyl elimination. Moreover, this reaction featured wide substrate scope, good functional group tolerance, and 100% atom economy.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-30
DOI
https://doi.org/10.1021/acs.joc.4c01332
Citations
6
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.50

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article

Palladium-Catalyzed Synthesis of β-Alkynyl Ketones via Selective 1,3-Alkynyl Migration of α,α-Disubstituted Allylic Alcohols

Runyou Ye, Yanqiong Zhang, Xiangge Zhou, Yang Long et al.
6 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
1.50
article

Palladium-Catalyzed Synthesis of β-Alkynyl Ketones via Selective 1,3-Alkynyl Migration of α,α-Disubstituted Allylic Alcohols

Runyou Ye, Yanqiong Zhang, Xiangge Zhou, Yang Long, Haoxiang Zhang, Qinyue Tao
article en
6 citations

Abstract

Herein, a palladium-catalyzed 1,3-alkynyl migration of allylic alcohol for the synthesis of β-alkynyl ketone was described. This intramolecular rearrangement reaction demonstrated an enhanced reactivity compared to the traditional intermolecular alkynylation by circumventing the dimerization of alkynes, exhibiting a specific selectivity toward β-alkynyl elimination. Moreover, this reaction featured wide substrate scope, good functional group tolerance, and 100% atom economy.

The Journal of Organic ChemistryVol. 89(18)
North Sichuan Medical University (CN), Sichuan University (CN)
National Natural Science Foundation of China, Department of Science and Technology of Sichuan Province
Openalex Percentile: Top 19%
Catalytic C–H Functionalization Methods
1.50
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Palladium-Catalyzed Synthesis of β-Alkynyl Ketones via Selective 1,3-Alkynyl Migration of α,α-Disubstituted Allylic Alcohols — Runyou Ye, Yanqiong Zhang, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS