Copper-Catalyzed Cross-Coupling of Allylboronic Acids with α-Diazoketones

被引：22
|
作者：
Das, Arindam [1 ]
Wang, Dong [1 ]
Belhomme, Marie-Charlotte [1 ]
Szabo, Kalman J. [1 ]
机构：
[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 19期
基金：
瑞典研究理事会;
关键词：
ALLYLIC BORONIC ESTERS; SECONDARY ALKYL CHLORIDES; STEREOSELECTIVE ALLYLATION; ONE-POT; ENANTIOSELECTIVE ALLYLBORATION; SELECTIVE FORMATION; ACTIVATED ENONES; DIAZO-COMPOUNDS; ARYL HALIDES; ALDEHYDES;
D O I：
10.1021/acs.orglett.5b02285
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper-catalyzed cross-coupling of substituted allylboronic acids with alpha-diazoketones was studied. This allylation reaction is highly regioselective, providing the branched allylic product. The process involves creation of a new C(sp(3))-C(sp(3)) bond by retaining the keto functional group of the alpha-diazoketone precursor.
引用
收藏
页码：4754 / 4757
页数：4
相关论文
共 50 条
  • [1] Copper-Catalyzed, Stereoselective Cross-Coupling of Cyclic Allyl Boronic Acids with α-Diazoketones
    Wang, Dong
    Szabo, Kalman J.
    [J]. ORGANIC LETTERS, 2017, 19 (07) : 1622 - 1625
  • [2] Mechanistic investigations of the transition-metal-catalyzed cross-coupling of allylboronic acids with α-diazoketones
    Wang, Dong
    Belhomme, Marie-Charlotte
    Szabo, Kalman
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [3] Copper-catalyzed cross-coupling of arylsulfonyl chlorides with arylboronic acids
    Hu, Feng
    Lei, Xiangyang
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [4] Copper-catalyzed decarboxylative cross-coupling of propiolic acids and terminal alkynes
    Yu, Miao
    Pan, Delin
    Jia, Wei
    Chen, Wei
    Jiao, Ning
    [J]. TETRAHEDRON LETTERS, 2010, 51 (09) : 1287 - 1290
  • [5] Copper-Catalyzed Decarboxylative Cross-Coupling of Carboxylic Acids and Arylcarbamoyl Chlorides
    Zhou, Dun
    Fan, Aihong
    Li, Xiang
    Chen, Chunxia
    Sun, Peng
    Peng, Jinsong
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (03) : 1146 - 1152
  • [6] Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling
    Arlow, Sophie I.
    Hartwig, John F.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) : 4567 - 4572
  • [7] Copper-Catalyzed Cross-Coupling of Arylacetylenes with Bromodifluoroacetamides
    Hu, Guo-Qin
    Yao, Li-Wei
    Gui, Shu-Sheng
    Geng, Chuang
    Zhang, Wen-Yan
    Liu, Jing-Hui
    Zhao, Bin
    [J]. SYNLETT, 2022, 33 (06) : 594 - 598
  • [8] C(sp 3)-C(sp 3) bond formation by transition-metal catalyzed cross-coupling of allylboronic acids with α-diazoketones
    Wang, Dong
    Belhomme, Marie-Charlotte
    Das, Arindam
    Szabo, Kalman
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [9] Formation of C(sp3)-C(sp3) Bonds by Palladium Catalyzed Cross-Coupling of α-Diazoketones and Allylboronic Acids
    Belhomme, Marie-Charlotte
    Wang, Dong
    Szabo, Kalman J.
    [J]. ORGANIC LETTERS, 2016, 18 (10) : 2503 - 2506
  • [10] Copper-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with aryl halides
    Zhao, Dongbing
    Gao, Chao
    Su, Xiaoyu
    He, Yunqing
    You, Jingsong
    Xue, Ying
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (47) : 9049 - 9051
12345