An efficient approach to access 1,1,2-triarylethanes enabled by the organo-photoredox-catalyzed decarboxylative addition reaction

被引:29
作者
Guo, Jing [1 ]
Huang, Gong-Bin [1 ]
Wu, Qiao-Lei [1 ]
Xie, Ying [1 ]
Weng, Jiang [1 ]
Lu, Gui [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab New Drug Design & Evaluat, Guangzhou 510006, Guangdong, Peoples R China
关键词
PARA-QUINONE METHIDES; ASYMMETRIC 1,6-CONJUGATE ADDITION; ALPHA-AMINO-ACIDS; C-H BONDS; VISIBLE-LIGHT; CARBOXYLIC-ACIDS; EOSIN Y; CONJUGATE ADDITIONS; QUATERNARY CENTERS; ARYL HALIDES;
D O I
10.1039/c9qo00380k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient protocol for the synthesis of 1,1,2-triarylethanes and 2,2-diarylethylamine with biological and pharmacological potential via organo-photoredox-catalyzed decarboxylative 1,6-conjugate addition of carboxylic acids to para-quinone methides has been developed. Different from the traditional transition-metal catalyzed multi-step synthetic strategy, our process involves a photoredox-promoted free radical pathway. A variety of structurally diverse products can be easily obtained under metal-free conditions in good to excellent yields (38 examples, up to 98% yield) in one step.
引用
收藏
页码:1955 / 1960
页数:6
相关论文
共 74 条
[1]   Photoredox-Induced Radical Relay toward Functionalized β-Amino Alcohol Derivatives [J].
An, Xiao-De ;
Jiao, Yon-Yon ;
Zhang, Hao ;
Gao, Yuxiang ;
Yu, Shouyun .
ORGANIC LETTERS, 2018, 20 (02) :401-404
[2]   A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis [J].
Andries, K ;
Verhasselt, P ;
Guillemont, J ;
Göhlmann, HWH ;
Neefs, JM ;
Winkler, H ;
Van Gestel, J ;
Timmerman, P ;
Zhu, M ;
Lee, E ;
Williams, P ;
de Chaffoy, D ;
Huitric, E ;
Hoffner, S ;
Cambau, E ;
Truffot-Pernot, C ;
Lounis, N ;
Jarlier, V .
SCIENCE, 2005, 307 (5707) :223-227
[3]   A Novel Iron-Catalyzed Decarboxylative Csp3-Csp2 Coupling of Proline Derivatives and Naphthol [J].
Bi, Hai-Peng ;
Chen, Wen-Wen ;
Liang, Yong-Min ;
Li, Chao-Jun .
ORGANIC LETTERS, 2009, 11 (15) :3246-3249
[4]   The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].
Bi, Hai-Peng ;
Zhao, Liang ;
Liang, Yong-Min ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795
[5]   Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids [J].
Capaldo, Luca ;
Buzzetti, Luca ;
Merli, Daniele ;
Fagnoni, Maurizio ;
Ravelli, Davide .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :7102-7109
[6]   A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes [J].
Caruana, Lorenzo ;
Kniep, Florian ;
Johansen, Tore Kiilerich ;
Poulsen, Pernille H. ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) :15929-15932
[7]   Modular Synthesis of Enantioenriched 1,1,2-Triarylethanes by an Enantioselective Arylboration and Cross-Coupling Sequence [J].
Chen, Bin ;
Cao, Peng ;
Yin, Xuemei ;
Liao, Yang ;
Jiang, Liyin ;
Ye, Jialin ;
Wang, Min ;
Liao, Jian .
ACS CATALYSIS, 2017, 7 (04) :2425-2429
[8]   Photoredox-Catalysed Decarboxylative Alkylation of N-Heteroarenes with N-(Acyloxy)phthalimides [J].
Cheng, Wan-Min ;
Shang, Rui ;
Fu, Ming-Chen ;
Fu, Yao .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (11) :2537-2541
[9]   Photoredox/Bronsted Acid Co-Catalysis Enabling Decarboxylative Coupling of Amino Acid and Peptide Redox-Active Esters with N-Heteroarenes [J].
Cheng, Wan-Min ;
Shang, Rui ;
Fu, Yao .
ACS CATALYSIS, 2017, 7 (01) :907-911
[10]   Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin [J].
Chu, Lingling ;
Ohta, Chisa ;
Zuo, Zhiwei ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) :10886-10889