Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction

Science China Chemistry

Volumn 54, Issue 6, 2011, Pages 951-956

  Wu, Hui ^a   Jin, Can ^a   Huang, Guoli ^a   Wang, Lianjun ^a   Jiang, Juli ^a   Wang, Leyong ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Heck reaction; imidazolinium salts; N heterocyclic carbenes; palladium

Indexed keywords

ACRYLAMIDES; ANCILLARY LIGANDS; BINAPHTHALENES; ETHYL ACRYLATES; HECK REACTIONS; IMIDAZOLINIUM SALTS; N-HETEROCYCLIC CARBENE LIGANDS; N-HETEROCYCLIC CARBENES; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS;

AMIDES; CARBON INORGANIC COMPOUNDS; CATALYSIS; CRYSTAL STRUCTURE; LIGANDS; SALTS; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

ORGANIC COMPOUNDS;

EID: 79958224008     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4272-4     Document Type: Article

References (34)

1. H.W. Wanzlick H.J. Schnherr 1968 Direct synthesis of a mercury salt-carbene complex Angew Chem 80 154 10.1002/ange.19680800411
2. K. Ofele 1968 1,3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer übergangsmetall-carben-komplex J Organomet Chem 12 42 43 10.1016/S0022-328X(00)88691-X
3. A.J. Arduengo III R.L. Harlow M. Kline 1991 A stable crystalline carbene J Am Chem Soc 113 361 363 10.1021/ja00001a054 1:CAS:528:DyaK3MXmt1Sjuw%3D%3D
4. W.A. Herrmann 2002 N-Heterocyclic carbenes: A new concept in organometallic catalysis Angew Chem Int Ed 41 1290 1309 10.1002/1521- 3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y 1:CAS:528: DC%2BD38Xjt1ertbY%3D (Pubitemid 34437411)
5. W.A. Herrmann C.P. Reisinger M. Spiegler 1998 Chelating N-heterocyclic carbene ligands in palladium-catalyzed Heck-type reactions J Organomet Chem 557 93 96 10.1016/S0022-328X(97)00736-5 1:CAS:528:DyaK1cXis1Oqsbo%3D (Pubitemid 128345433)
6. J.C. Garrison W.J. Youngs 2005 Ag(I) N-heterocyclic carbene complexes: synthesis, structure, and application Chem Rev 105 3978 4008 10.1021/cr050004s 1:CAS:528:DC%2BD2MXhtFyrtbjJ (Pubitemid 41724067)
7. D. Bourissou O. Guerret F.P. Gabbai G. Bertrand 2000 Stable carbenes Chem Rev 100 39 92 10.1021/cr940472u 1:CAS:528:DyaK1MXotVemu7w%3D
8. D. Enders T. Balensiefer 2004 Nucleophilic carbenes in asymmetric organocatalysis Acc Chem Res 37 534 541 10.1021/ar030050j 1:CAS:528: DC%2BD2cXisVequ7Y%3D
9. J.S. Johnson 2004 Catalyzed reactions of acyl anion equivalents Angew Chem Int Ed 43 1326 1328 10.1002/anie.200301702 1:CAS:528:DC%2BD2cXivFSksLg%3D (Pubitemid 39257907)
10. K. Zeitler 2005 Extending mechanistic routes in heterazolium catalysis promising concepts for versatile synthetic methods Angew Chem Int Ed 44 7506 7510 10.1002/anie.200502617 1:CAS:528:DC%2BD2MXhtlalsbzM (Pubitemid 41713708)
11. D. Enders O. Niemeier A. Henseler 2007 Organocatalysis by N-heterocyclic carbenes Chem Rev 107 5606 5655 10.1021/cr068372z 1:CAS:528:DC%2BD2sXht1SgtbjJ
12. N. Marion S. Díez-González S.P. Nolan 2007 N-Heterocyclic carbenes as organocatalysts Angew Chem Int Ed 46 2988 3000 10.1002/anie. 200603380 1:CAS:528:DC%2BD2sXltVSmt7c%3D (Pubitemid 46973507)
13. H. Clavier S.P. Nolan 2007 N-Heterocyclic carbene and phosphine ruthenium indenylidene precatalysts: A comparative study in olefin metathesis Chem Eur J 13 8029 8036 10.1002/chem.200700256 1:CAS:528:DC%2BD2sXhtFOqtrjF (Pubitemid 47556376)
14. M.C. Perry K. Burgess 2003 Chiral N-heterocyclic carbene-transition metal complexes in asymmetric catalysis Tetrahedron: Asymm 14 951 961 10.1016/S0957-4166(03)00037-5 1:CAS:528:DC%2BD3sXisleis7k%3D (Pubitemid 36398349)
15. A.J. Arduengo III H.V. Rasika R.L. Harlow M. Kline 1992 Electronic stabilization of nucleophilic carbenes J Am Chem Soc 114 5530 5534 10.1021/ja00040a007 1:CAS:528:DyaK38Xkt1KnsLc%3D
16. L. Pu 1998 1,1′-Binaphthyl dimers, oligomers, and polymers: Molecular recognition, asymmetric catalysis, and new materials Chem Rev 98 2405 2494 10.1021/cr970463w 1:CAS:528:DyaK1cXmtlKgs74%3D
17. Q. Xu W. L. Duan Z.Y. Lei Z.B. Zhu M. Shi 2005 A novel cis-chelated Pd(II)-NHC complex for catalyzing Suzuki and Heck-type crosscoupling reactions Tetrahedron 61 11225 11229 10.1016/j.tet.2005.09.010 1:CAS:528: DC%2BD2MXhtFKgu7bI (Pubitemid 41502901)
18. T. Chen J. Gao M. Shi 2006 A novel tridentate NHC-Pd(II) complex and its application in the Suzuki and Heck-type cross-coupling reactions Tetrahedron 62 6289 6294 10.1016/j.tet.2006.04.034 1:CAS:528:DC%2BD28Xlt12nt7Y%3D
19. T. Chen X. G. Liu M. Shi 2007 Synthesis of new NHC-rhodium and irid ium complexes derived from 2,2′-diaminobiphenyl and their catalytic activities toward hydrosilylation of ketones Tetrahedron 63 4874 4880 10.1016/j.tet.2007. 03.150 1:CAS:528:DC%2BD2sXkvFyrt7c%3D (Pubitemid 46669640)
20. T. Zhang M. Shi M. Zhao 2008 Bis(NHC)-Pd(II) complexes as highly efficient catalysts for allylation of aldehydes with allyltributyltin Tetrahedron 64 2412 2418 10.1016/j.tet.2008.01.017 1:CAS:528: DC%2BD1cXhsFajsLw%3D
21. T. Zhang W. Wang X. Gu M. Shi 2008 N-Heterocyclic carbene sulfonamide palladium complexes and their catalytic activities in suzukimiyaura coupling reaction Organometallics 27 753 757 10.1021/om701030z 1:CAS:528: DC%2BD1cXhsV2nsLw%3D (Pubitemid 351364128)
22. Z. Liu T. Zhang M. Shi 2008 Cyclometalated cis-chelated bidentate Nheterocyclic carbene palladium complexes: Synthetic, structural, and catalytic studies Organometallics 27 2668 2671 10.1021/om800069p 1:CAS:528: DC%2BD1cXkvVChu74%3D
23. A.R. Chianese R.H. Crabtree 2005 Axially chiral bidentate N-heterocyclic carbene ligands derived from binam: rhodium and iridium complexes in asymmetric ketone hydrosilylation Organometallics 24 4432 4436 10.1021/om050323+ 1:CAS:528:DC%2BD2MXmslelsLw%3D (Pubitemid 41321857)
24. J.J. Van-Veldhuizen S.B. Garber J.S. Kingsbury A.H. Hoveyda 2002 A recyclable chiral Ru catalyst for enantioselective olefin metathesis. Efficient catalytic asymmetric ring-opening/cross metathesis in air J Am Chem Soc 124 4954 4955 10.1021/ja020259c 1:CAS:528:DC%2BD38XivVOmtro%3D (Pubitemid 34495877)
25. J. J. Van-Veldhuizen D.G. Gillingham S.B. Garber O. Kataoka A. H. Hoveyda 2003 Chiral Ru-based complexes for asymmetric olefin metathesis: Enhancement of catalyst activity through steric and electronic modifications J Am Chem Soc 125 12502 12508 10.1021/ja0302228 1:CAS:528:DC%2BD3sXntlymtLY%3D (Pubitemid 37254766)
26. A.O. Larsen W. Leu C.N. Oberhuber J.E. Campbell A.H. Hoveyda 2004 Bidentate NHC-based chiral ligands for efficient Cu-catalyzed enantioselective allylic alkylations: Structure and activity of an air-stable chiral Cu complex J Am Chem Soc 126 11130 11131 10.1021/ja046245j 1:CAS:528:DC%2BD2cXms1Oqu74%3D (Pubitemid 39223168)
27. D.S. Clyne J. Jin E. Genest J.C. Gallucci T.V. RajanBabu 2000 First chelated chiral N-heterocyclic bis-carbene complexes Org Lett 2 1125 1128 10.1021/ol005694v 1:CAS:528:DC%2BD3cXhvFKntLs%3D
28. B. Gadenne P. Hesemann J.J. Moreau 2005 Easily recoverable BINOL ligand with ionic tag for asymmetric catalysis Tetrahedron: Asymm 16 2001 2006 10.1016/j.tetasy.2005.04.013 1:CAS:528:DC%2BD2MXltFSmsb0%3D (Pubitemid 40804414)
29. Q.S. Lu L. Dong J. Zhang J. Li L. Jiang Y. Huang S. Qin C.W. Hu X.Q. Yu 2009 Imidazolium-functionalized BINOL as a multifunctional receptor for chromogenic and chiral anion recognition Org Lett 11 669 672 10.1021/ol8027303 1:CAS:528:DC%2BD1MXmtFOntg%3D%3D
30. P. Wipf J.K. Jung 2000 Formal total synthesis of (+)-diepoxin σ J Org Chem 65 6319 6337 10.1021/jo000684t 1:CAS:528:DC%2BD3cXmt1KnsL0%3D
31. K. Ito M. Takahashi T. Hoshino M. Nishiki Y. Ohba 2006 Study on host-guest complexation of anions based on 2,2′-dihydroxyl-1,1′- binaphtalene derivatives Lett Org Chem 3 735 740 10.2174/157017806779025898 1:CAS:528:DC%2BD2sXktFSn (Pubitemid 44941890)
32. G. Occhipinti H.R. Bjørsvik K.W. Törnroos A. Fürstner V.R. Jensen 2007 The first imidazolium-substituted metal alkylidene Organometallics 26 4383 4385 10.1021/om700590v 1:CAS:528:DC%2BD2sXotFSmsbs%3D (Pubitemid 47389090)
33. Q.X. Liu L.N. Yin J.C. Feng 2007 New N-heterocyclic carbene silver(I) and mercury(II) 2-D supramolecular layers by the π-π stacking interactions J Organomet Chem 692 3655 3663 10.1016/j.jorganchem.2007.05.005 1:CAS:528:DC%2BD2sXnslKlu74%3D (Pubitemid 47042807)
34. Sheldrick GM, SHELXL-97, Universität Göttingen, Göttingen, Germany, 1998