Palladium-Catalyzed Intermolecular [4+1] Spiroannulation by C(sp3)-H Activation and Naphthol Dearomatization

被引：75
作者：
Tan, Bojun [1 ]
Bai, Lu [1 ]
Ding, Pin [1 ]
Liu, Jingjing [1 ]
Wang, Yaoyu [1 ]
Luan, Xinjun [1 ,2 ]
机构：
[1] Northwest Univ, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Coll Chem & Mat Sci, Xian 710127, Shaanxi, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 05期
基金：
美国国家科学基金会;
关键词：
C-H activation; cyclization; dearomatization; palladium; spiro compounds; C-H ACTIVATION; ASYMMETRIC ALLYLIC DEAROMATIZATION; C(SP(2))-H BOND ACTIVATION; ARYL IODIDES; AROMATIC FUNCTIONALIZATION; EFFICIENT SYNTHESIS; METHOXY GROUPS; ALKYLATION; ANNULATION; ALKYNES;
D O I：
10.1002/anie.201813202
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel palladium-catalyzed [4+1] spiroannulation was developed by using a C(sp(3))-H activation/naphthol dearomatization approach. This bimolecular domino reaction of two aryl halides was realized through a sequence of cyclometallation-facilitated C(sp(3))-H activation, biaryl cross-coupling, and naphthol dearomatization, thus rendering the rapid assembly of a new class of spirocyclic molecules in good yields with broad functional-group tolerance. Preliminary mechanistic studies indicate that C-H cleavage is likely involved in the rate-determining step, and a five-membered palladacycle was identified as the key intermediate for the intermolecular coupling.
引用
收藏
页码：1474 / 1478
页数：5
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