Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed Umpolung 1,4-Addition of Aryl Iodides to Enals

被引：85

作者：

Yang, Wenjun ^{[1
]}

Ling, Bo ^{[1
]}

Hu, Bowen ^{[2
]}

Yin, Haolin ^{[2
]}

Mao, Jianyou ^{[1
]}

Walsh, Patrick J. ^{[2
]}

机构：

[1] Nanjing Tech Univ, Inst Adv Synth, Sch Chem & Mol Engn, 30 South Puzhu Rd, Nanjing 211816, Peoples R China

[2] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, 231 South 34th St, Philadelphia, PA 19104 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 01期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

addition reactions; cooperative catalysis; N-heterocyclic carbenes; palladium; umpolung; ASYMMETRIC ALLYLIC ALKYLATION; AZA-BENZOIN REACTION; ACID BINARY-SYSTEM; COOPERATIVE CATALYSIS; RELAY CATALYSIS; STEREOSELECTIVE-SYNTHESIS; HOMOENOLATE ADDITIONS; GAMMA-BUTYROLACTONES; CONJUGATE ADDITION; ALPHA-ALLYLATION;

D O I：

10.1002/anie.201912584

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An umpolung 1,4-addition of aryl iodides to enals promoted by cooperative (terpy)Pd/NHC catalysis was developed that generates various bioactive beta,beta-diaryl propanoate derivatives. This system is not only the first reported palladium-catalyzed arylation of NHC-bound homoenolates but also expands the scope of NHC-induced umpolung transformations. A diverse array of functional groups such as esters, nitriles, alcohols, and heterocycles are tolerated under the mild conditions. This method also circumvents the use of moisture-sensitive organometallic reagents.

引用

页码：161 / 166

页数：6

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