Ruthenium-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Aryl and Trifluoromethyl Group Substituted Unsymmetrical Internal Alkynes

被引:63
|
作者
Kawatsura, Motoi [1 ]
Namioka, Junya [1 ]
Kajita, Koji [1 ]
Yamamoto, Mitsuaki [1 ]
Tsuji, Hiroaki [1 ]
Itoh, Toshiyuki [1 ]
机构
[1] Tottori Univ, Grad Sch Engn, Dept Chem & Biotechnol, Tottori 6808552, Japan
关键词
MARKOVNIKOV TRANS-ADDITION; ENOL-ESTER SYNTHESIS; TERMINAL ALKYNES; VINYLIDENE COMPLEXES; DIMERIZATION; BOND;
D O I
10.1021/ol201238u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regio- and stereoselective addition of carboxylic acids to aryl and trifluoromethyl group substituted unsymmetrical Internal alkynes has been accomplished: the Ru-3(CO)(12)/3PPh(3) catalyst system has effectively catalyzed the reaction to afford the trifluoromethyl group substituted (E)-enol esters with high regio- and stereoselectivities.
引用
收藏
页码:3285 / 3287
页数:3
相关论文
共 50 条
  • [1] Regio- and stereoselective addition of carboxylic acids to phenylacetylene catalyzed by cyclopentadienyl ruthenium complexes
    Ye, SM
    Leong, WK
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (06) : 1117 - 1120
  • [2] Structure-Selectivity Relationship in Ruthenium-Catalyzed Regio- and Stereoselective Addition of Alkynes to Pyrazoles: An Experimental and Theoretical Investigation
    Das, Uttam Kumar
    Mandal, Subhajit
    Anoop, Anakuthil
    Bhattacharjee, Manish
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21): : 9979 - 9991
  • [3] Enol Ester Synthesis via Cobalt-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Alkynes
    Chen, Jia-Feng
    Li, Changkun
    [J]. ORGANIC LETTERS, 2018, 20 (21) : 6719 - 6724
  • [4] Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of aryl carbamates with alkynes via C-H bond activation
    Reddy, Mallu Chenna
    Jeganmohan, Masilamani
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (05) : 481 - 483
  • [5] Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether
    Babu, Madala Hari
    Kumar, Gadi Ranjith
    Kant, Ruchir
    Reddy, Maddi Sridhar
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (27) : 3894 - 3897
  • [6] Silver-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Ynol Ethers
    Yin, Jing
    Bai, Yihui
    Mao, Mengyi
    Zhu, Gangguo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19): : 9179 - 9185
  • [7] Ruthenium-Catalyzed Regioselective [2+2+2] Cyclotrimerization of Trifluoromethyl Group Substituted Internal Alkynes
    Kawatsura, Motoi
    Yamamoto, Mitsuaki
    Namioka, Junya
    Kajita, Koji
    Hirakawa, Takuya
    Itoh, Toshiyuki
    [J]. ORGANIC LETTERS, 2011, 13 (05) : 1001 - 1003
  • [8] Palladium-Catalyzed Regio- and Stereoselective Hydroaminocarbonylation of Unsymmetrical Internal Alkynes toward α,β-Unsaturated Amides
    Kuai, Chang-Sheng
    Xu, Jian-Xing
    Chen, Bo
    Wu, Xiao-Feng
    [J]. ORGANIC LETTERS, 2022, 24 (24) : 4464 - 4469
  • [9] Ru(II)-Catalyzed Difunctional Pyridyloxy-Directed Regio- and Stereospecific Addition of Carboxylic Acids to Internal Alkynes
    Wang, Qin
    Shi, Yan
    Huang, Xiaoli
    Wang, Yongzhuang
    Jiao, Jiao
    Tang, Yuhai
    Li, Jing
    Xu, Silong
    Li, Yang
    [J]. ORGANIC LETTERS, 2022, 24 (01) : 379 - 384
  • [10] Ruthenium-catalyzed oxidative cleavage of alkynes to carboxylic acids
    Yang, D
    Chen, F
    Dong, ZM
    Zhang, DW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06): : 2221 - 2223