Recent quinone diazide based transformations via metal-carbene formation

被引：26
作者：
Bera, Satabdi [1 ]
Sarkar, Souradip [1 ]
Samanta, Rajarshi [1 ]
机构：
[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India
来源：
NEW JOURNAL OF CHEMISTRY | 2021年 / 45卷 / 23期
关键词：
C-H FUNCTIONALIZATION; NATURAL-PRODUCTS; PHOSPHORUS LIGANDS; 6+3 CYCLOADDITION; ARYLATION; ACTIVATION; ACID; REARRANGEMENT; CONSTRUCTION; ATROPISOMERS;
D O I：
10.1039/d1nj01678d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The diazo quinone or quinone diazide class of compounds has been extensively utilised to introduce phenol/naphthol moieties into hydrocarbons or nitrogen-containing heterocycles under transition metal catalysis. The reactions proceed via C-H insertion or migratory insertion of metal carbenes. In many cases, the site-selectivities were obtained via the guidance of directing groups. Various rearrangement reactions were explored with the metal carbenes generated from these diazo compounds. Further, interesting asymmetric reactions were studied to obtain phenol/naphthol containing compounds having stereogenic centers or axial chirality with high enantioselectivity. In this review, the recent progress on synthetic studies of metal carbenes generated from quinone diazide moieties has been summarized.
引用
收藏
页码：10135 / 10149
页数：15
相关论文
共 88 条
  • [1] 3-Naphthylindole Construction by Rhodium(II)-Catalyzed Regioselective Direct Arylation of Indoles with 1-Diazonaphthalen-2-(1H)-ones
    Baral, Ek Raj
    Lee, Yong Rok
    Kim, Sung Hong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (13) : 2883 - 2892
  • [2] FORMATION OF 6(2H)-ACEANTHRYLENONES AND THEIR PHOTOCHEMICAL CONVERSION INTO ACEANTHRYLENES
    BECKER, HD
    ELEBRING, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) : 1319 - 1322
  • [3] ARYL DIAZO-COMPOUNDS AND DIAZONIUM SALTS AS POTENTIAL IRREVERSIBLE PROBES OF THE GAMMA-AMINOBUTYRIC-ACID RECEPTOR
    BOUCHET, MJ
    RENDON, A
    WERMUTH, CG
    GOELDNER, M
    HIRTH, C
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (12) : 2222 - 2227
  • [4] Indole, a core nucleus for potent inhibitors of tubulin polymerization
    Brancale, Andrea
    Silvestri, Romano
    [J]. MEDICINAL RESEARCH REVIEWS, 2007, 27 (02) : 209 - 238
  • [5] Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products
    Bringmann, Gerhard
    Gulder, Tanja
    Gulder, Tobias A. M.
    Breuning, Matthias
    [J]. CHEMICAL REVIEWS, 2011, 111 (02) : 563 - 639
  • [6] Atropochiral C,X- and C,C-Chelating Carbon Ligands
    Canac, Yves
    Chauvin, Remi
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (16) : 2325 - 2335
  • [7] Rh(III)-Catalyzed C-H Activation/Cyclization of Benzamides and Diazonaphthalen-2(1H)-ones for Synthesis of Lactones
    Chen, Renjie
    Cui, Sunliang
    [J]. ORGANIC LETTERS, 2017, 19 (15) : 4002 - 4005
  • [8] Modified BINOL ligands in asymmetric catalysis
    Chen, Y
    Yekta, S
    Yudin, AK
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 3155 - 3211
  • [9] The Challenge of Atropisomerism in Drug Discovery
    Clayden, Jonathan
    Moran, Wesley J.
    Edwards, Paul J.
    LaPlante, Steven R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (35) : 6398 - 6401
  • [10] Quinone Diazides for Olefin Functionalization
    Dao, Hai T.
    Baran, Phil S.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) : 14382 - 14386
123456789