Autoxidation Photoredox Catalysis for the Synthesis of 2-Phosphinoylindoles

被引:78
作者
Wang, Chun-Hai [1 ]
Li, Yong-Hong [1 ]
Yang, Shang-Dong [1 ,2 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
关键词
PHOSPHORUS-CENTERED RADICALS; VISIBLE-LIGHT PHOTOCATALYSIS; C-P; RING-CLOSURE; DIPHENYLPHOSPHINE OXIDE; MERGING PHOTOREDOX; CYCLIZATION; INDOLE; PHOSPHORYLATION; ALKYNES;
D O I
10.1021/acs.orglett.8b00722
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new approach to the synthesis of 2-phosphinoylindoles through photoredox catalysis without external oxidants has been developed. Promoted by a ruthenium photoredox catalyst, a broad scope of 2-phosphinoylindoles can be synthesized through phosphinoylation/cyclization of diphenylphosphine oxide at room temperature under irradiation without external oxidants. The estrone skeleton isocyan is also an amenable substrate for this cyclization, yielding a molecule that has potential medicinal applications.
引用
收藏
页码:2382 / 2385
页数:4
相关论文
共 73 条
  • [1] Rules for Anionic and Radical Ring Closure of Alkynes
    Alabugin, Igor V.
    Gilmore, Kerry
    Manoharan, Mariappan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) : 12608 - 12623
  • [2] Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors
    Alexandre, Francois-Rene
    Amador, Agnes
    Bot, Stephanie
    Caillet, Catherine
    Convard, Thierry
    Jakubik, Jocelyn
    Musiu, Chiara
    Poddesu, Barbara
    Vargiu, Luana
    Liuzzi, Michel
    Roland, Arlene
    Seifer, Maria
    Standring, David
    Storer, Richard
    Dousson, Cyril B.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) : 392 - 395
  • [3] RULES FOR RING-CLOSURE - APPLICATION TO INTRAMOLECULAR ALDOL CONDENSATIONS IN POLYKETONIC SUBSTRATES
    BALDWIN, JE
    LUSCH, MJ
    [J]. TETRAHEDRON, 1982, 38 (19) : 2939 - 2947
  • [4] RULES FOR RING-CLOSURE - RING FORMATION BY CONJUGATE ADDITION OF OXYGEN NUCLEOPHILES
    BALDWIN, JE
    THOMAS, RC
    KRUSE, LI
    SILBERMAN, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) : 3846 - 3852
  • [5] 3,3′-bis(diphenylphosphino)-1,1′-disubstituted-2,2′-biindoles:: Easily accessible, electron-rich, chiral diphosphine ligands for homogeneous enantioselective hydrogenation of oxoesters
    Benincori, T
    Piccolo, O
    Rizzo, S
    Sannicolò, F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) : 8340 - 8347
  • [6] Development and validation of a sensitive LC-MS/MS method with electrospray ionization for quantitation of zafirlukast, a selective leukotriene antagonist in human plasma: application to a clinical pharmacokinetic study
    Bharathi, D. Vijaya
    Naidu, A.
    Jagadeesh, B.
    Laxmi, K. N. K. Maha
    Laxmi, P. Revathi Naga
    Reddy, Pandu Ranga
    Mullangi, Ramesh
    [J]. BIOMEDICAL CHROMATOGRAPHY, 2008, 22 (06) : 645 - 653
  • [7] Synthesis of a 2-indolylphosphonamide derivative with inhibitory activity against yersiniabactin biosynthesis
    Bisseret, Philippe
    Thielges, Sabine
    Stephane, Bourg
    Miethke, Marcus
    Marahiel, Mohamed A.
    Eustache, Jacques
    [J]. TETRAHEDRON LETTERS, 2007, 48 (35) : 6080 - 6083
  • [8] 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
  • [9] Photoredox/Bronsted Acid Co-Catalysis Enabling Decarboxylative Coupling of Amino Acid and Peptide Redox-Active Esters with N-Heteroarenes
    Cheng, Wan-Min
    Shang, Rui
    Fu, Yao
    [J]. ACS CATALYSIS, 2017, 7 (01): : 907 - 911
  • [10] Cismesia MA, 2015, CHEM SCI, V6, P5426, DOI 10.1039/c5sc02185e