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
[1]  
Amatore C, 2001, CHEM-EUR J, V7, P2134, DOI 10.1002/1521-3765(20010518)7:10<2134::AID-CHEM2134>3.0.CO
[2]  
2-9
[3]  
[Anonymous], CRYSTALSTRUCTURE 4 1
[4]  
[Anonymous], CRYSTALCLEAR DAT COL
[5]  
[Anonymous], 2020, CRYSALISPRO DAT COLL
[6]   Bulky triarylarsines are effective ligands for palladium catalysed Heck olefination [J].
Baber, RA ;
Collard, S ;
Hooper, M ;
Orpen, AG ;
Pringle, PG ;
Wilkinson, MJ ;
Wingad, RL .
DALTON TRANSACTIONS, 2005, (08) :1491-1498
[7]   One-pot palladium-catalyzed cross-coupling reaction of aryl iodides with stannylarsanes and stannylstibanes [J].
Bonaterra, M ;
Martín, SE ;
Rossi, RA .
ORGANIC LETTERS, 2003, 5 (15) :2731-2734
[8]   Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes [J].
Bourne, Samuel L. ;
O'Brien, Matthew ;
Kasinathan, Sivarajan ;
Koos, Peter ;
Tolstoy, Paeivi ;
Hu, Dennis X. ;
Bates, Roderick W. ;
Martin, Benjamin ;
Schenkel, Berthold ;
Ley, Steven V. .
CHEMCATCHEM, 2013, 5 (01) :159-172
[9]   SIR2011: a new package for crystal structure determination and refinement [J].
Burla, Maria Cristina ;
Caliandro, Rocco ;
Camalli, Mercedes ;
Carrozzini, Benedetta ;
Cascarano, Giovanni Luca ;
Giacovazzo, Carmelo ;
Mallamo, Mariarosaria ;
Mazzone, Annamaria ;
Polidori, Giampiero ;
Spagna, Riccardo .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2012, 45 :357-361
[10]   Stille Polycondensation for Synthesis of Functional Materials [J].
Carsten, Bridget ;
He, Feng ;
Son, Hae Jung ;
Xu, Tao ;
Yu, Luping .
CHEMICAL REVIEWS, 2011, 111 (03) :1493-1528