Transition-Metal-Free Cross-Coupling by Using Tertiary Benzylic Organoboronates

被引：21
|
作者：
Takeda, Mitsutaka [1 ]
Nagao, Kazunori [1 ]
Ohmiya, Hirohisa [1 ,2 ]
机构：
[1] Kanazawa Univ, Div Pharmaceut Sci, Grad Sch Med Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan
[2] PRESTO, JST, 4-1-8 Honcho, Kawaguchi, Saitama 3320012, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 50期
关键词：
cross-coupling; quaternary carbon centers; alkylation; tertiary alkylboronates; transition-metal-free; VICARIOUS NUCLEOPHILIC-SUBSTITUTION; ALPHA-BORYL CARBANIONS; AROMATIC-SUBSTITUTION; ATE COMPLEXES; ARYL; BOND; ARYLATION; SECONDARY; NITRILES; ESTERS;
D O I：
10.1002/anie.202010251
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The transition-metal-free cross-coupling of alkyl or aryl electrophiles by using tertiary benzylic organoboronates is reported. This reaction involves the generation of tertiary alkyl anions from organoboronates in the presence of an alkoxide base and then their substitution reactions. This protocol allows the simple and efficient construction of quaternary carbon centers.
引用
收藏
页码：22460 / 22464
页数：5
相关论文
共 50 条
  • [1] Transition-metal-free cross-coupling reaction of benzylic halides with arylboronic acids leading to diarylmethanes
    Ueda, Mitsuhiro
    Nakakoji, Daiki
    Kuwahara, Yuki
    Nishimura, Kota
    Ryu, Ilhyong
    [J]. TETRAHEDRON LETTERS, 2016, 57 (37) : 4142 - 4144
  • [2] Transition-Metal-Free Cross-Coupling of Aryl and N-Heteroaryl Cyanides with Benzylic Zinc Reagents
    Quinio, Pauline
    Roman, Daniela Sustac
    Leon, Thierry
    William, Sharankini
    Karaghiosoff, Konstantin
    Knochel, Paul
    [J]. ORGANIC LETTERS, 2015, 17 (17) : 4396 - 4399
  • [3] Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes
    He, Qing
    Wang, Liwen
    Liang, Yong
    Zhang, Zunting
    Wnuk, Stanislaw F.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9422 - 9427
  • [4] Transition-metal-free regioselective cross-coupling of BODIPYs with thiols
    Lv, Fan
    Tang, Bing
    Hao, Erhong
    Liu, Qingyun
    Wang, Hua
    Jiao, Lijuan
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (11) : 1639 - 1642
  • [5] Photocatalyzed Transition-Metal-Free Oxidative Cross-Coupling Reactions of Tetraorganoborates**
    Music, Arif
    Baumann, Andreas N.
    Boser, Florian
    Mueller, Nicolas
    Matz, Florian
    Jagau, Thomas C.
    Didier, Dorian
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (13) : 4322 - 4326
  • [6] Synthesis of α-aryl ketones through transition-metal-free cross-coupling
    [J]. Nature Synthesis, 2023, 2 : 1138 - 1139
  • [7] Synthesis of α-aryl ketones through transition-metal-free cross-coupling
    Li, Xue
    Song, Qiuling
    [J]. NATURE SYNTHESIS, 2023, 2 (12): : 1138 - 1139
  • [8] Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles
    Li, Chengxi
    Zhang, Yuanyuan
    Sun, Qi
    Gu, Tongnian
    Peng, Henian
    Tang, Wenjun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10774 - 10777
  • [9] Transition-Metal-Free Oxidative Cross-Coupling of Tetraarylborates to Biaryls Using Organic Oxidants
    Gerleve, Carolin
    Studer, Armido
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (36) : 15468 - 15473
  • [10] Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines
    Gil-Negrete, Jose M.
    Perez Sestelo, Jose
    Sarandeses, Luis A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (15): : 9778 - 9785
12345