Synthesis of Fused Pyran Derivatives via Visible-Light-Induced Cascade Cyclization of 1,7-Enynes with Acyl Chlorides

被引:111
作者
Li, Chen-Guang [1 ]
Xu, Guo-Qjang [1 ]
Xu, Peng-Fei [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
关键词
DIASTEREOSELECTIVE SYNTHESIS; DECARBOXYLATIVE ARYLATION; N-ARYLACRYLAMIDES; CARBOXYLIC-ACIDS; PHOTOREDOX; FUNCTIONALIZATION; ANNULATION; ACYLARYLATION; CONSTRUCTION; AZAPHILONES;
D O I
10.1021/acs.orglett.6b03684
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A photocatalytic cascade cyclization of 1,7-enynes with acyl chlorides has been established. This method offers an operationally simple access to diverse fused pyran derivatives with a broad substrate scope in high yields from simple acyl chlorides via an acyl radical intermediate.
引用
收藏
页码:512 / 515
页数:4
相关论文
共 55 条
  • [1] Visible-Light-Mediated Photocatalytic Difunctionalization of Olefins by Radical Acylarylation and Tandem Acylation/Semipinacol Rearrangement
    Bergonzini, Giulia
    Cassani, Carlo
    Lorimer-Olsson, Haldor
    Horberg, Johanna
    Wallentin, Carl-Johan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (10) : 3292 - 3295
  • [2] Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis
    Bergonzini, Giulia
    Cassani, Carlo
    Wallentin, Carl-Johan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14066 - 14069
  • [3] Chemistry of acyl radicals
    Chatgilialoglu, C
    Crich, D
    Komatsu, M
    Ryu, I
    [J]. CHEMICAL REVIEWS, 1999, 99 (08) : 1991 - 2069
  • [4] Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond
    Chen, Jia-Rong
    Hu, Xiao-Qiang
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) : 1911 - 1923
  • [5] Photoredox-Induced Functionalization of Alkenes for the Synthesis of Substituted Imidazolines and Oxazolidines
    Chen, Jian-Qiang
    Yu, Wan-Lei
    Wei, Yun-Long
    Li, Teng-Hui
    Xu, Peng-Fei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01) : 243 - 249
  • [6] Intramolecular 1,5-H transfer reaction of aryl iodides through visible-light photoredox catalysis: a concise method for the synthesis of natural product scaffolds
    Chen, Jian-Qiang
    Wei, Yun-Long
    Xu, Guo-Qiang
    Liang, Yong-Min
    Xu, Peng-Fei
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (38) : 6455 - 6458
  • [7] Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of -Oxo Acids
    Chu, Lingling
    Lipshultz, Jeffrey M.
    MacMillan, David W. C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) : 7929 - 7933
  • [8] Chudasama V, 2010, NAT CHEM, V2, P592, DOI [10.1038/nchem.685, 10.1038/NCHEM.685]
  • [9] Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions
    de Arriba, Angel L. Fuentes
    Urbitsch, Felix
    Dixon, Darren J.
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (100) : 14434 - 14437
  • [10] A family of luminescent coordination compounds: iridium(III) polyimine complexes
    Dixon, IM
    Collin, JP
    Sauvage, JP
    Flamigni, L
    Encinas, S
    Barigelletti, F
    [J]. CHEMICAL SOCIETY REVIEWS, 2000, 29 (06) : 385 - 391