Enantioselective Dearomative Mizoroki-Heck Reaction of Naphthalenes

被引：25

作者：

Han, Xiao-Qing ^{[1
]}

Wang, Lei ^{[2
]}

Yang, Ping ^{[3
]}

Liu, Jing-Yuan ^{[1
]}

Xu, Wei-Yan ^{[1
]}

Zheng, Chao ^{[3
]}

Liang, Ren-Xiao ^{[1
]}

You, Shu-Li ^{[3
]}

Zhang, Junliang ^{[2
]}

Jia, Yi-Xia ^{[1
,3
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310014, Peoples R China

[2] Fudan Univ, Dept Chem, Shanghai 200438, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ACS CATALYSIS | 2022年 / 12卷 / 01期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; dearomatization; naphthalene; Mizoroki-Heck reaction; palladium; CATALYTIC ASYMMETRIC DEAROMATIZATION; INDOLES; ARYLATION; ACCESS; PHENOL; ARYL;

D O I：

10.1021/acscatal.1c05008

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A palladium-catalyzed intramolecular enantioselective Mizoroki-Heck reaction of naphthalenes has been developed via dearomative migratory insertion of an endocyclic pi-bond of naphthalene, followed by delta-hydride elimination. This reaction relies on the use of chiral sulfonamide phosphine type Xu-Phos ligand, which successfully inhibits the competitive and undesired C-H arylation reaction and efficiently promotes the formation of spirooxindole and spiroisoindolin-1-one products. Synthetic transformations of the product afford a series of unique heterocyclic compounds with enantiomeric excess (ee) values retained.

引用

页码：655 / 661

页数：7

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