Ruthenium(II)-Catalyzed C-H Alkynylation of Weakly Coordinating Benzoic Acids

被引:55
作者
Mei, Ruhuai [1 ]
Zhang, Shou-Kun [1 ]
Ackermann, Lutz [1 ]
机构
[1] Georg August Univ, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
基金
欧洲研究理事会;
关键词
CATALYZED DIRECT ALKYNYLATION; CARBOXYLIC-ACIDS; C(SP(3))-H BONDS; ARYLATION; ARENES; ARYL; FUNCTIONALIZATION; ACTIVATION; HYDROARYLATION; ALKYNES;
D O I
10.1021/acs.orglett.7b01294
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-H alkynylations with weakly coordinating aide accomplished by the aid of an expedient ruthenium(II) catalysis manifold. The user-friendly C-H alkynylation occurred under mild conditions with the weak base K2CO3. The versatility of the ruthenium(II) catalysis was reflected by providing;step-economical access to phthalides as well as enabling unprecedented decarboxylative ortho-C-H alkynylations.
引用
收藏
页码:3171 / 3174
页数:4
相关论文
共 76 条
[41]   Ni(II)-catalyzed dehydrative alkynylation of unactivated (hetero) aryl C-H bonds using oxygen: a user-friendly approach [J].
Liu, Yan-Hua ;
Liu, Yue-Jin ;
Yan, Sheng-Yi ;
Shi, Bing-Feng .
CHEMICAL COMMUNICATIONS, 2015, 51 (58) :11650-11653
[42]   A sustainable and simple catalytic system for direct alkynylation of C(sp2)-H bonds with low nickel loadings [J].
Liu, Yue-Jin ;
Liu, Yan-Hua ;
Yan, Sheng-Yi ;
Shi, Bing-Feng .
CHEMICAL COMMUNICATIONS, 2015, 51 (29) :6388-6391
[43]   Ruthenium(II)-Catalyzed Oxidative C-H Alkenylations of Sulfonic Acids, Sulfonyl Chlorides and Sulfonamides [J].
Ma, Wenbo ;
Mei, Ruhuai ;
Tenti, Giammarco ;
Ackermann, Lutz .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (46) :15248-15251
[44]   Nickel- and Copper-Catalyzed Direct Alkynylation of Azoles and Polyfluoroarenes with Terminal Alkynes under O2 or Atmospheric Conditions [J].
Matsuyama, Naoto ;
Kitahara, Masanori ;
Hirano, Koji ;
Satoh, Tetsuya ;
Miura, Masahiro .
ORGANIC LETTERS, 2010, 12 (10) :2358-2361
[45]   Nickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl Bromides [J].
Matsuyama, Naoto ;
Hirano, Koji ;
Satoh, Tetsuya ;
Miura, Masahiro .
ORGANIC LETTERS, 2009, 11 (18) :4156-4159
[46]   Ruthenium(II)-catalyzed C-H functionalizations on benzoic acids with aryl, alkenyl and alkynyl halides by weak-O-coordination [J].
Mei, Ruhuai ;
Zhu, Cuiju ;
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2016, 52 (89) :13171-13174
[47]   Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C-H Functionalization Sequences [J].
Mesganaw, Tehetena ;
Ellman, Jonathan A. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (09) :1097-1104
[48]   Direct (Hetero)arylation Polymerization: Simplicity for Conjugated Polymer Synthesis [J].
Pouliot, Jean-Remi ;
Grenier, Francois ;
Blaskovits, J. Terence ;
Beaupre, Serge ;
Leclerc, Mario .
CHEMICAL REVIEWS, 2016, 116 (22) :14225-14274
[49]   Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups [J].
Rouquet, Guy ;
Chatani, Naoto .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) :11726-11743
[50]   Manganese-Catalyzed C-H Alkynylation: Expedient Peptide Synthesis and Modification [J].
Ruan, Zhixiong ;
Sauermann, Nicolas ;
Manoni, Elisabetta ;
Ackermann, Lutz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) :3172-3176