Palladium-catalyzed carbon-carbon bond cleavage of primary alcohols: decarbonylative coupling of acetylenic aldehydes with haloarenes

被引:0
作者
Jin, Zewei [1 ]
Li, Qiang [1 ]
Zhu, Maoshuai [1 ]
Zhang, Yanqiong [1 ]
Yan, Xufei [2 ,3 ]
Zhou, Xiangge [1 ]
机构
[1] Sichuan Univ, Coll Chem, 29 Wangjiang Rd, Chengdu 610064, Peoples R China
[2] Sichuan Univ, West China Sch Publ Hlth, Chengdu 610041, Peoples R China
[3] Sichuan Univ, West China Hosp 4, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
INTERNAL ALKYNES; C-C; ACTIVATION; DIARYLACETYLENES; ELIMINATION; CYCLIZATION; LIBERATION;
D O I
10.1039/d5ra00357a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the current work, a palladium-catalyzed C-C bond cleavage reaction of primary alcohols has been developed. This transformation was characterized by a broad substrate scope, superior functional group tolerance, and high efficiency for selective C-C bond cleavage and was then followed by alkynyl-aryl cross coupling. Mechanism studies indicated that the propargyl alcohols underwent beta-H elimination to form aldehydes rather than having undergone beta-C elimination. The corresponding aldehyde intermediates then proceeded through a decarbonylation and coupling reaction with haloarenes to yield diarylacetylenes.
引用
收藏
页码:7826 / 7831
页数:6
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