Visible-light induced cross-electrophile coupling of imines and anhydrides to synthesize α-amino ketones

被引:3
作者
Cao, Renxu [1 ,2 ]
Liu, Yu [1 ,2 ]
Shi, Xiaoxin [1 ,2 ]
Zheng, Jun [1 ,2 ]
机构
[1] East China Univ Sci & Technol, Minist Educ, Engn Res Ctr Pharmaceut Proc Chem, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
关键词
PHOTOREDOX CATALYSIS; ASYMMETRIC HYDROGENATION; AMINATION; ALCOHOLS; DERIVATIVES; RADICALS; ALKYLATION; ARYLATION; ALDEHYDES;
D O I
10.1039/d3cc03028h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
alpha-Amino ketones are important motifs in synthetic and medicinal chemistry. Efficient methods to directly access these motifs from feasible precursors are, however, limited. Herein, a visible-light mediated reductive cross-electrophile coupling of readily available imines and anhydrides was developed. Under mild reaction conditions, the umpolung reactivity of diverse imines engaged with anhydrides gives a variety of alpha-amino ketones with good yields and a broad functional group compatibility. Primary mechanistic studies revealed that this transformation might proceed through a radical-radical cross coupling pathway dominantly.
引用
收藏
页码:10668 / 10671
页数:4
相关论文
共 62 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   Recent advances in the synthesis of α-amino ketones [J].
Allen, Lewis A. T. ;
Raclea, Robert-Cristian ;
Natho, Philipp ;
Parsons, Philip J. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (03) :498-513
[3]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF A KETOMETHYLENE ANALOG OF A TRIPEPTIDE INHIBITOR OF ANGIOTENSIN CONVERTING ENZYME [J].
ALMQUIST, RG ;
CHAO, WR ;
ELLIS, ME ;
JOHNSON, HL .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (12) :1392-1398
[4]   Photocatalytic Late-Stage C-H Functionalization [J].
Bellotti, Peter ;
Huang, Huan-Ming ;
Faber, Teresa ;
Glorius, Frank .
CHEMICAL REVIEWS, 2023, 123 (08) :4237-4352
[5]   ESTIMATION OF EXCITED-STATE REDOX POTENTIALS BY ELECTRON-TRANSFER QUENCHING - APPLICATION OF ELECTRON-TRANSFER THEORY TO EXCITED-STATE REDOX PROCESSES [J].
BOCK, CR ;
CONNOR, JA ;
GUTIERREZ, AR ;
MEYER, TJ ;
WHITTEN, DG ;
SULLIVAN, BP ;
NAGLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4815-4824
[6]   Heteroannulation of arynes with N-aryl-α-aminoketones for the synthesis of unsymmetrical N-aryl-2,3-disubstituted indoles: an aryne twist of Bischler-Mohlau indole synthesis [J].
Bunescu, Ala ;
Piemontesi, Cyril ;
Wang, Qian ;
Zhu, Jieping .
CHEMICAL COMMUNICATIONS, 2013, 49 (87) :10284-10286
[7]   Visible-Light -Triggered Directly Reductive Arylation of Carbonyl/Iminyl Derivatives through Photocatalytic PCET [J].
Chen, Ming ;
Zhao, Xinxin ;
Yang, Chao ;
Xia, Wujiong .
ORGANIC LETTERS, 2017, 19 (14) :3807-3810
[8]   Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions [J].
de Arriba, Angel L. Fuentes ;
Urbitsch, Felix ;
Dixon, Darren J. .
CHEMICAL COMMUNICATIONS, 2016, 52 (100) :14434-14437
[9]   Visible-light photoredox catalyzed hydroacylation of electron-deficient alkenes: carboxylic anhydride as an acyl radical source [J].
Dong, Shupeng ;
Wu, Guibing ;
Yuan, Xiaoqian ;
Zou, Chuncheng ;
Ye, Jinxing .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11) :2230-2234
[10]   Visible light-promoted CO2 fixation with imines to synthesize diaryl α-amino acids [J].
Fan, Xinyuan ;
Gong, Xu ;
Ma, Mengyue ;
Wang, Rui ;
Walsh, Patrick J. .
NATURE COMMUNICATIONS, 2018, 9