Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical

被引：54
作者：
Cao, Jia [1 ,3 ]
Wang, Guoqiang [1 ]
Gao, Liuzhou [1 ]
Cheng, Xu [2 ]
Li, Shuhua [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, Inst Theoret & Computat Chem, Key Lab Mesoscop Chem,Minist Educ, Nanjing 210093, Jiangsu, Peoples R China
[2] Nanjing Univ, Sch Chem & Chem Engn, Inst Chem & Biomed Sci, Jiangsu Key Lab Adv Organ Mat, Nanjing 210093, Jiangsu, Peoples R China
[3] Yanan Univ, Sch Chem & Chem Engn, Yanan 716000, Peoples R China
来源：
CHEMICAL SCIENCE | 2018年 / 9卷 / 15期
基金：
中国博士后科学基金; 中国国家自然科学基金;
关键词：
HETEROCYCLIC CARBENE BORANES; ENANTIOENRICHED HOMOPROPARGYLIC ALCOHOLS; POLARITY-REVERSAL CATALYSIS; C-C BOND; PHOSPHINE-BORANES; VISIBLE-LIGHT; CARBONYL PROPARGYLATION; TRANSFER HYDROGENATION; ORGANIC-SYNTHESIS; STABLE RADICALS;
D O I：
10.1039/c7sc05225a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A pyridine-boryl radical promoted reductive coupling reaction of aldehydes with 1,1-diarylethylenes has been established via a combination of computational and experimental studies. Density functional theory calculations and control experiments suggest that the ketyl radical from the addition of the pyridine-boryl radical to aldehydes is the key intermediate for this C-C bond formation reaction. This metal-free reductive coupling reaction features a broad substrate scope and good functional compatibility.
引用
收藏
页码：3664 / 3671
页数：8
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共 82 条
  • [1] Transition metal catalyzed element-element' additions to alkynes
    Ansell, Melvyn B.
    Navarro, Oscar
    Spencer, John
    [J]. COORDINATION CHEMISTRY REVIEWS, 2017, 336 : 54 - 77
  • [2] Synthesis and Characterization of B-Heterocyclic π-Radical and Its Reactivity as a Boryl Radical
    Aramaki, Yoshitaka
    Orniya, Hideki
    Yamashita, Makoto
    Nakabayashi, Koji
    Ohkoshi, Shin-ichi
    Nozaki, Kyoko
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (49) : 19989 - 19992
  • [3] LIGATED BORYL RADICALS .2. ELECTRON-SPIN RESONANCE STUDIES OF TRIALKYLAMINE BORYL RADICALS
    BABAN, JA
    MARTI, VPJ
    ROBERTS, BP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (11): : 1723 - 1733
  • [4] Phosphine-boranes as selective reagents for the radical deoxygenation of a hindered secondary alcohol
    Barton, DHR
    Jacob, M
    [J]. TETRAHEDRON LETTERS, 1998, 39 (11) : 1331 - 1334
  • [5] Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes
    Beletskaya, Irina
    Moberg, Christina
    [J]. CHEMICAL REVIEWS, 2006, 106 (06) : 2320 - 2354
  • [6] Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene
    Bower, John F.
    Patman, Ryan L.
    Krische, Michael J.
    [J]. ORGANIC LETTERS, 2008, 10 (05) : 1033 - 1035
  • [7] Transition-Metal-Free, Visible-Light-Enabled Decarboxylative Borylation of Aryl N-Hydroxyphthalimide Esters
    Candish, Lisa
    Teders, Michael
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (22) : 7440 - 7443
  • [8] Recent developments in the chemistry of amine- and phosphine-boranes
    Carboni, B
    Monnier, L
    [J]. TETRAHEDRON, 1999, 55 (05) : 1197 - 1248
  • [9] Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons
    Chen, Dongping
    Xu, Guangqing
    Zhou, Qinghai
    Chung, Lung Wa
    Tang, Wenjun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) : 9767 - 9770
  • [10] Isonicotinate Ester Catalyzed Decarboxylative Borylation of (Hetero)Aryl and Alkenyl Carboxylic Acids through N-Hydroxyphthalimide Esters
    Cheng, Wan-Min
    Shang, Rui
    Zhao, Bin
    Xing, Wei-Long
    Fu, Yao
    [J]. ORGANIC LETTERS, 2017, 19 (16) : 4291 - 4294
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