Ruthenium-Catalyzed C-C Coupling of Fluorinated Alcohols with Allenes: Dehydrogenation at the Energetic Limit of β-Hydride Elimination

被引：47
|
作者：
Sam, Brannon [1 ]
Luong, Tom [1 ]
Krische, Michael J. [1 ]
机构：
[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 18期
关键词：
allylic compounds; diastereoselectivity; fluorine; hydrogenation; ruthenium; TRIFLUOROMETHYLATED ALLYLIC ALCOHOLS; ASYMMETRIC FLUORINATION; TRANSFER HYDROGENATION; REVERSE PRENYLATION; GRIGNARD-REAGENTS; REDUCING ACTION; CARBONYL; PARAFORMALDEHYDE; CROTYLATION; ALLYLATION;
D O I：
10.1002/anie.201500238
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Ruthenium(II) complexes catalyze the C-C coupling of 1,1-disubstituted allenes and fluorinated alcohols to form homoallylic alcohols bearing all-carbon quaternary centers with good to complete levels of diastereoselectivity. Whereas fluorinated alcohols are relatively abundant and tractable, the corresponding aldehydes are often not commercially available because of their instability.
引用
收藏
页码：5465 / 5469
页数：5
相关论文
共 50 条
  • [41] Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction
    Ambler, Brett R.
    Turnbull, Ben W. H.
    Suravarapu, Sankar Rao
    Uteuliyev, Maulen M.
    Huynh, Nancy O.
    Krische, Michael J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (29) : 9091 - 9094
  • [42] Alkyne-Aldehyde Reductive C-C Coupling through Ruthenium-Catalyzed Transfer Hydrogenation: Direct Regio- and Stereoselective Carbonyl Vinylation to Form Trisubstituted Allylic Alcohols in the Absence of Premetallated Reagents
    Leung, Joyce C.
    Patman, Ryan L.
    Sam, Brannon
    Krische, Michael J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (44) : 12437 - 12443
  • [43] Redox-Triggered Ruthenium-Catalyzed Remote C-H Acylation with Primary Alcohols
    Guo, Xiao
    Wu, Yang
    Li, Gongqiang
    Xia, Ji-Bao
    ACS CATALYSIS, 2020, 10 (21): : 12987 - 12995
  • [44] Rhodium(III)-Catalyzed C-C Coupling of Arenes with 2-Vinyloxiranes: Synthesis of Allylic Alcohols
    Yu, Songjie
    Li, Xingwei
    ORGANIC LETTERS, 2014, 16 (04) : 1200 - 1203
  • [45] Formation of C-C Bonds via Ruthenium-catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level
    Shibahara, Fumitoshi
    Krische, Michael J.
    CHEMISTRY LETTERS, 2008, 37 (11) : 1102 - 1107
  • [46] DFT study on the ruthenium-catalyzed decarbonylative annulation of an alkyne with a six-membered hydroxychromone via C-H/C-C activation
    Long, Hong-Jing
    Zhang, Lei
    Lian, Bing
    Fang, De-Cai
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (04): : 1056 - 1064
  • [47] Ruthenium-Catalyzed Chemo-Selective Carbene Insertion into C-H Bond of Styrene over Cyclopropanation: C-C Bond Formation
    Jayarani, Arumugam
    Deepa, Masilamani
    Khan, Hilal Ahmad
    Koothradan, Fathima Febin
    Yoganandhini, Sekar
    Sreelakshmi, Vinod
    Sivasankar, Chinnappan
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (22): : 15817 - 15831
  • [48] Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides
    Lee, Jeong Min
    Bae, Dae Young
    Park, Jin Yong
    Jo, Hwi Yul
    Lee, Eunsung
    Rhee, Young Ho
    Park, Jaiwook
    ORGANIC LETTERS, 2020, 22 (12) : 4608 - 4613
  • [49] Ruthenium-Catalyzed Aromatic C-H Activation of Benzylic Alcohols via Remote Electronic Activation
    Watson, Andrew J. A.
    Maxwell, Aoife C.
    Williams, Jonathan M. J.
    ORGANIC LETTERS, 2010, 12 (17) : 3856 - 3859
  • [50] Synthesis of 2-alkoxy-5-methylenetetrahydropyrans: A regioselective ruthenium-catalyzed C-C coupling reaction of prop-2-yn-1-ols with allyl alcohol
    Derien, S
    Ropartz, L
    Le Paih, J
    Dixneuf, PH
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10): : 3524 - 3531
12345