Synthesis and Structure of Organobismuth Chlorides and Triflates Containing (C,E)-Chelating Ligands (E=O, S) and Their Catalytic Application in the Allylation of Aldehydes with Tetraallyltin

被引:11
作者
Tan, Nianyuan [1 ,2 ]
Chen, Yi [1 ,3 ]
Zhou, Yongbo [1 ]
Au, Chak-Tong [1 ,4 ]
Yin, Shuang-Feng [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemobiosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
[2] Hunan Inst Engn, Coll Chem & Chem Engn, Xiangtan 411104, Peoples R China
[3] Hunan Univ Chinese Med, Sch Basic Med, Changsha 410208, Hunan, Peoples R China
[4] Hong Kong Baptist Univ, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
aldehydes; allylation; bismuth; chelates; hypervalent compounds; HIGHLY EFFICIENT; PINCER COMPLEX; ORGANOANTIMONY; COORDINATION; REACTIVITY; DIHALIDES; SURFACES; ACIDITY; SULFUR;
D O I
10.1002/cplu.201300288
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Four air-stable hypervalent organobismuth compounds with (C,O)- or (C,S)-chelating ligands, namely, R2BiCl (R=2-(MeECH2)C6H4; E=O (3), S (4)), [2-(MeOCH2)C6H4](2)BiOTf (5), and [{2-(MeSCH2)C6H4}(2)Bi][OTf] (6; OTf=triflate) were successfully synthesized. The structures of compounds3-6 were determined by single-crystal X-ray diffraction. Compound6 comprises the [2-(MeSCH2)C6H4](2)Bi+ cation and the OTf- anion. Compounds5 exhibited good catalytic efficiency and reusability for the allylation reaction of different aldehydes with tetraallyltin in methanol to give the corresponding homoallylic alcohols in excellent yields.
引用
收藏
页码:1363 / 1369
页数:7
相关论文
共 49 条
[31]  
Sheldrick G.M., 1997, SADABS, Empirical Absorption Correction Program
[32]   A short history of SHELX [J].
Sheldrick, George M. .
ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 :112-122
[33]   5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocines:: Highly reactive and recoverable organobismuth reagents for cross-coupling reactions with aryl bromides [J].
Shimada, S ;
Yamazaki, O ;
Tanaka, T ;
Rao, MLN ;
Suzuki, Y ;
Tanaka, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (16) :1845-1848
[34]  
Shimada S., 2003, ANGEW CHEM, V115, P1889
[35]   Recent Advances in the Synthesis and Application of Bismuth-Containing Heterocyclic Compounds [J].
Shimada, Shigeru .
CURRENT ORGANIC CHEMISTRY, 2011, 15 (05) :601-620
[36]   Oxidative Addition of Diphenyldichalcogenides PhEEPh (E = S, Se, Te) to Low-Valent CN- and NCN-Chelated Organoantimony and Organobismuth Compounds [J].
Simon, Petr ;
Jambor, Roman ;
Ruzicka, Ales ;
Dostal, Libor .
ORGANOMETALLICS, 2013, 32 (01) :239-248
[37]   Monomeric Organoantimony(I) and Organobismuth(I) Compounds Stabilized by an NCN Chelating Ligand: Syntheses and Structures [J].
Simon, Petr ;
de Proft, Frank ;
Jambor, Roman ;
Ruzicka, Ales ;
Dostal, Libor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5468-5471
[38]   Organobismuth(III) dihalides with T-shaped geometry stabilized by intramolecular N→Bi interactions and related diorganobismuth(III) halides [J].
Soran, Albert P. ;
Silvestru, Cristian ;
Breunig, Hans J. ;
Balazs, Gabor ;
Green, Jennifer C. .
ORGANOMETALLICS, 2007, 26 (05) :1196-1203
[39]   Unexpected formation of highly stabilized tetrakis(2-alkoxyphenyl)bismuthonium salts in the oxidation of tris-(2-alkoxyphenyl)bismuthanes with iodosylbenzene [J].
Suzuki, H ;
Ikegami, T ;
Azuma, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1609-1616
[40]   NCN Chelated Organoantimony(III) and Organobismuth(III) Phosphinates and Phosphites: Synthesis, Structure and Reactivity [J].
Svoboda, Tomas ;
Jambor, Roman ;
Ruzicka, Ales ;
Padelkova, Zdenka ;
Erben, Milan ;
Dostal, Libor .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (33) :5222-5230