Accessing Furan-Linked Methylene Oxindoles/Benzofurans via Stereoselective Palladium-Catalyzed Domino Cyclization/Cycloisomerization

被引：2
|
作者：
Yi, Yujie [1 ]
Yuan, Ye [2 ]
Zhu, Songsong [3 ]
Wang, Jinbei [1 ]
Wang, Zhaolin [1 ]
Zhang, Jingli [1 ]
Gao, Guanbin [1 ,2 ]
Sun, Taolei [1 ,2 ]
机构：
[1] Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, Hubei Key Lab Nanomed Neurodegenerat Dis, Wuhan 430070, Peoples R China
[2] Wuhan Univ Technol, State Key Lab Adv Technol Mat Synth & Proc, Wuhan 430070, Peoples R China
[3] Hubei Prov Inst Food Supervis & Test, Wuhan 430075, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 17期
基金：
中国国家自然科学基金;
关键词：
EFFICIENT SYNTHESIS; 1,2-ALLENYL KETONES; CYCLIZATION; DERIVATIVES; OXINDOLE; ACIDS; ARYL;
D O I：
10.1021/acs.joc.4c00895
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed domino cyclization/cycloisomerization reaction of alkyne-tethered carbamoyl chlorides with (E)-beta-chloroenones is reported. This reaction proceeds via a syn-carbopalladation of the alkyne, followed by a vinyl-PdII-catalyzed cycloisomerization of the (E)-beta-chloroenone cascade, which provides an efficient method to synthesize furan-linked methylene oxindoles. The reaction features stereodefined vinyl-PdII species, high to excellent 5-exo/6-endo selectivity, excellent Z/E selectivity, and the sequential formation of three bonds and bis-heterocycles. The strategy for the synthesis of furan-containing benzofurans has also been demonstrated.
引用
收藏
页码：12085 / 12093
页数：9
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