Cobalt-Catalyzed Diastereoselective Difluoroalkylation/Giese Addition Domino Reactions

被引：42
|
作者：
Han, Shengnan [1 ]
Liu, Shaodong [1 ]
Liu, Lei [1 ]
Ackermann, Lutz [2 ]
Li, Jie [1 ]
机构：
[1] Jiangnan Univ, Sch Pharmaceut Sci, Lihu Rd 1800, Wuxi 214122, Jiangsu, Peoples R China
[2] Georg August Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 14期
基金：
中国国家自然科学基金;
关键词：
RAUHUT-CURRIER REACTION; ENANTIOSELECTIVE DESYMMETRIZATION; ARYLATIVE CYCLIZATION; CYCLOHEXADIENONES; ACCESS; FLUORINE; MONO; DIFLUOROMETHYLATION; TRANSFORMATIONS; DEAROMATIZATION;
D O I：
10.1021/acs.orglett.9b01400
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient cobalt-catalyzed difluoroalkylation/Giese radical conjugate cyclization manifold with various alkyne-tethered cyclohexadienones and halogenated fluorinating reagents was accomplished under remarkable mild reaction conditions, thus providing an expedient route to valuable fluorinated chromens. The utility of this transformation was demonstrated by high site selectivity as well as chemo- and diastereoselectivity, broad substrate scope, excellent functional group tolerance, and facile late-stage modification.
引用
收藏
页码：5387 / 5391
页数：5
相关论文
共 50 条
  • [21] Cobalt-Catalyzed Cross Addition of Silylacetylenes to Internal Alkynes
    Sakurada, Tetsuya
    Sugiyama, Yu-ki
    Okamoto, Sentaro
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 3583 - 3591
  • [22] Cobalt-catalyzed conjugate addition of silylacetylenes to α,β-unsaturated ketones
    Nishimura, Takahiro
    Sawano, Takahiro
    Ou, Keiyu
    Hayashi, Tamio
    CHEMICAL COMMUNICATIONS, 2011, 47 (36) : 10142 - 10144
  • [23] Cobalt-catalyzed highly diastereoselective [3+2] carboannulation reactions: facile access to substituted indane derivatives
    Dey, Arnab
    Singh, Anurag
    Volla, Chandra M. R.
    CHEMICAL COMMUNICATIONS, 2022, 58 (09) : 1386 - 1389
  • [24] Recent advances and prospects in the cobalt-catalyzed amination reactions
    Saranya, Padinjare Veetil
    Neetha, Mohan
    Philip, Rose Mary
    Anilkumar, Gopinathan
    TETRAHEDRON, 2022, 104
  • [25] Highly chemoselective cobalt-catalyzed biaryl coupling reactions
    Guelak, Samet
    Stepanek, Ondrej
    Malberg, Jennifer
    Rad, Babak Rezaei
    Kotora, Martin
    Wolf, Robert
    Jacobi von Wangelin, Axel
    CHEMICAL SCIENCE, 2013, 4 (02) : 776 - 784
  • [26] COBALT-CATALYZED AND COBALT-UNCATALYZED REACTIONS OF DIYNES WITH ACTIVATED ALKENES
    ZHOU, ZM
    BATTAGLIA, LP
    CHIUSOLI, GP
    COSTA, M
    NARDELLI, M
    PELIZZI, C
    PREDIERI, G
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (22) : 1632 - 1634
  • [27] Understanding the Mechanisms of Cobalt-Catalyzed Hydrogenation and Dehydrogenation Reactions
    Zhang, Guoqi
    Vasudevan, Kalyan V.
    Scott, Brian L.
    Hanson, Susan K.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (23) : 8668 - 8681
  • [28] Cobalt-catalyzed diastereoselective reductive [3+2] cycloaddition of allenes and enones
    Chang, Hong-Tai
    Jayanth, Thiruvellore Thatai
    Cheng, Chien-Hong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (14) : 4166 - +
  • [29] Modular Diastereoselective Construction of Polysubstituted Cyclopentanes Enabled by Cobalt-Catalyzed Arylfluoroalkylation of Cyclopentenes
    Wang, Ming-Kuan
    Luo, Yun-Cheng
    Zhao, Hai-Yang
    Zhang, Yanxia
    Zhang, Dawei
    Zhang, Xingang
    ACS CATALYSIS, 2023, 13 (21) : 14090 - 14102
  • [30] Diastereoselective cobalt-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant
    Lam, Hon Wai
    Joensuu, Pekka M.
    Murray, Gordon J.
    Fordyce, Euan A. F.
    Prieto, Oscar
    Luebbers, Thomas
    ORGANIC LETTERS, 2006, 8 (17) : 3729 - 3732
12345