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

共 106 条

[21]

Dugal-Tessier J., 2012, ANGEW CHEM, V124, P5047

[22] An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones [J].

Dugal-Tessier, Julien ;

O'Bryan, Elizabeth A. ;

Schroeder, Thomas B. H. ;

Cohen, Daniel T. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) :4963-4967

[23]

Fang, 2011, ANGEW CHEM, V123, P11986

[24] Enantioselective Stetter Reactions of Enals and Modified Chalcones Catalyzed by N-Heterocyclic Carbenes [J].

Fang, Xinqiang ;

Chen, Xingkuan ;

Lv, Hui ;

Chi, Yonggui Robin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (49) :11782-11785

[25] N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union [J].

Fortman, George C. ;

Nolan, Steven P. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5151-5169

[26]

Fu ZQ, 2013, NAT CHEM, V5, P835, DOI [10.1038/nchem.1710, 10.1038/NCHEM.1710]

[27] Enantioselective N-Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium [J].

Gillard, Rachel M. ;

Fernando, Jared E. M. ;

Lupton, David W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (17) :4712-4716

[28]

GILLARD RM, 2018, ANGEW CHEM, V130, P4802, DOI DOI 10.1021/ACS.ORGLETT.9B00198

[29]

Grossmann A., 2012, Angew. Chem, V124, P320, DOI DOI 10.1002/ANIE.201105415

[30] N-Heterocyclic Carbene Catalyzed Domino Reactions [J].

Grossmann, Andre ;

Enders, Dieter .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) :314-325

← 1 2 3 4 5 6 7 8 9 10 →