Tertiary arsine ligands for the Stille coupling reaction

被引:10
作者
Chishiro, Akane [1 ]
Konishi, Masafumi [1 ]
Inaba, Ryoto [1 ]
Yumura, Takashi [2 ]
Imoto, Hiroaki [1 ]
Naka, Kensuke [1 ,3 ]
机构
[1] Kyoto Inst Technol, Fac Mol Chem & Engn, Sakyo Ku, Goshokaido Cho, Kyoto 6068585, Japan
[2] Kyoto Inst Technol, Grad Sch Sci & Technol, Fac Mat Sci & Technol, Sakyo Ku, Kyoto 6068585, Japan
[3] Kyoto Inst Technol, Mat Innovat Lab, Sakyo Ku, Goshokaido Cho, Kyoto 6068585, Japan
关键词
OXIDATIVE ADDITION; COMPLEXES BEARING; PALLADIUM; TRIPHENYLARSINE; MECHANISMS; CHEMISTRY; CHLORIDES; ENERGIES; DFT;
D O I
10.1039/d1dt02955j
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The Stille coupling reaction is one of the most important coupling reactions. It is well known that the triphenylarsine ligand can accelerate the reaction rate of Stille coupling. However, other arsine ligands have never been investigated for the Stille coupling reaction so far. In this work, we prepared 13 kinds of C-3-symmetrical tertiary arsine ligands and discovered that tri(p-anisyl)arsine is the best ligand for the reaction of tributylvinyltin and p-iodoanisole. The reaction mechanism was studied by dispersion-corrected density functional theory calculations to demonstrate the energetic feasibility of the Stille coupling reactions mediated by tri(p-anisyl)arsine.
引用
收藏
页码:95 / 103
页数:9
相关论文
共 43 条
[11]   Carbonylative C-C Bond Activation of Electron-Poor Cyclopropanes: Rhodium-Catalyzed (3+1+2) Cycloadditions of Cyclopropylamides [J].
Dalling, Andrew G. ;
Yamauchi, Takayuki ;
McCreanor, Niall G. ;
Cox, Lydia ;
Bower, John F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (01) :221-225
[12]   The mechanisms of the Stille reaction [J].
Espinet, P ;
Echavarren, AM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (36) :4704-4734
[13]   η2-dba complexes of Pd(0):: The substituent effect in Suzuki-Miyaura coupling [J].
Fairlamb, IJS ;
Kapdi, AR ;
Lee, AF .
ORGANIC LETTERS, 2004, 6 (24) :4435-4438
[14]   PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY [J].
FARINA, V ;
KRISHNAN, B ;
MARSHALL, DR ;
ROTH, GP .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5434-5444
[15]   PALLADIUM CATALYSIS IN CEPHALOSPORIN CHEMISTRY - GENERAL METHODOLOGY FOR THE SYNTHESIS OF CEPHEM SIDE-CHAINS [J].
FARINA, V ;
BAKER, SR ;
BENIGNI, DA ;
HAUCK, SI ;
SAPINO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5833-5847
[16]   LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].
FARINA, V ;
KRISHNAN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595
[17]   Pd2(dba)3•CHCl3/AsPh3 -: a powerful catalyst system for Pd(0)-mediated C-C-bond formation [J].
Faust, R ;
Gobelt, B .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1998, 340 (01) :90-93
[18]   Organometallic reactivity: the role of metal-ligand bond energies from a computational perspective [J].
Fey, Natalie ;
Ridgway, Benjamin M. ;
Jover, Jesus ;
McMullin, Claire L. ;
Harvey, Jeremy N. .
DALTON TRANSACTIONS, 2011, 40 (42) :11184-11191
[19]   AROMATIC FLUORODERIVATIVES .95. THE INVESTIGATION OF THE BEHAVIOR OF THE POLYFLUOROAROMATIC COMPOUNDS CONTAINING GROUP VA ELEMENTS IN ACID-MEDIA [J].
FURIN, GG ;
KRUPODER, SA ;
REZVUKHIN, AI ;
KILINA, TM ;
YAKOBSON, GG .
JOURNAL OF FLUORINE CHEMISTRY, 1983, 22 (04) :345-375
[20]   Synthesis, properties and application of electronically-tuned tetraarylarsonium salts as phase transfer catalysts (PTC) for the synthesis of gem-difluorocyclopropanes [J].
Grudzien, Krzysztof ;
Basak, Tymoteusz ;
Barbasiewicz, Michal ;
Wojciechowski, Tomasz M. ;
Fedorynski, Michal .
JOURNAL OF FLUORINE CHEMISTRY, 2017, 197 :106-110