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Volumn 7, Issue , 2011, Pages 555-564

Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis

Author keywords

Chiral mono(N heterocyclic carbene) complex; Heck Mizoroki reaction; Hydroamination; Suzuki Miyaura reaction

Indexed keywords


EID: 79955915987     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.7.64     Document Type: Article
Times cited : (37)

References (101)
  • 1
    • 33750044837 scopus 로고    scopus 로고
    • N-heterocyclic carbenes as ligands for high-oxidation-state metal complexes and oxidation catalysis
    • Glorius, F., Ed.; Topics in Organometallic Chemistry, Springer: Berlin Heidelberg, doi:10.1007/3418-025
    • Rogers, M. M.; Stahl, S. S. N-Heterocyclic Carbenes as Ligands for High-Oxidation-State Metal Complexes and Oxidation Catalysis. In N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry, Vol. 21; Springer: Berlin Heidelberg, 2007. doi:10.1007/3418-025
    • (2007) N-Heterocyclic Carbenes in Transition Metal Catalysis , vol.21
    • Rogers, M.M.1    Stahl, S.S.2
  • 2
    • 79955881596 scopus 로고    scopus 로고
    • N-heterocyclic carbenes as ligands for high-oxidation-state metal complexes and oxidation catalysis
    • Springer: Berlin Heidelberg, doi:10.1007/11603795
    • Glorius, F., Ed. N-Heterocyclic Carbenes as Ligands for High-Oxidation-State Metal Complexes and Oxidation Catalysis; Topics in Organometallic Chemistry, Vol. 21; Springer: Berlin Heidelberg, 2007. doi:10.1007/11603795
    • (2007) Topics in Organometallic Chemistry , vol.21
    • Glorius, F.1
  • 3
    • 68949156547 scopus 로고    scopus 로고
    • doi: 10.1021/cr900241h
    • Arduengo, A. J.; Bertrand, G. Chem. Rev. 2009, 109, 3209-3210. doi:10.1021/cr900241h
    • (2009) Chem. Rev. , vol.109 , pp. 3209-3210
    • Arduengo, A.J.1    Bertrand, G.2
  • 6
    • 68949154627 scopus 로고    scopus 로고
    • doi: 10.1021/cr8005203
    • Arnold, P. L.; Casely, I. J. Chem. Rev. 2009, 109, 3599-3611. doi:10.1021/cr8005203
    • (2009) Chem. Rev. , vol.109 , pp. 3599-3611
    • Arnold, P.L.1    Casely, I.J.2
  • 7
  • 9
    • 49649084986 scopus 로고    scopus 로고
    • doi: 10.1002/ange.200703883
    • Hahn, F. E.; Jahnke, M. C. Angew. Chem. 2008, 120, 3166-3216. doi:10.1002/ange.200703883
    • (2008) Angew. Chem. , vol.120 , pp. 3166-3216
    • Hahn, F.E.1    Jahnke, M.C.2
  • 10
    • 53049091364 scopus 로고    scopus 로고
    • doi: 10.1002/anie.200703883
    • Angew. Chem., Int. Ed. 2008, 47, 3122-3172. doi:10.1002/anie.200703883
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3122-3172
  • 12
    • 33846869728 scopus 로고    scopus 로고
    • doi: 10.1016/j.ccr.2006.08.001
    • Pugh, D.; Danopoulos, A. A. Coord. Chem. Rev. 2007, 251, 610-641. doi:10.1016/j.ccr.2006.08.001
    • (2007) Coord. Chem. Rev. , vol.251 , pp. 610-641
    • Pugh, D.1    Danopoulos, A.A.2
  • 13
    • 27744442656 scopus 로고    scopus 로고
    • Rhenium and technetium complexes with N-heterocyclic carbenes - A review
    • DOI 10.1016/j.jorganchem.2005.07.014, PII S0022328X05005395, Carbene Chemistry
    • Braband, H.; Kückmann, T. I.; Abram, U. J. Organomet. Chem. 2005, 690, 5421-5429. doi:10.1016/j.jorganchem.2005.07.014 (Pubitemid 41635889)
    • (2005) Journal of Organometallic Chemistry , vol.690 , Issue.24-25 , pp. 5421-5429
    • Braband, H.1    Kuckmann, T.I.2    Abram, U.3
  • 14
    • 0001075235 scopus 로고    scopus 로고
    • doi: 10.1002/1521-3757(20020415)114:8<1342::AID-ANGE1342>3.0.C O;2-A
    • Herrmann, W. A. Angew. Chem. 2002, 114, 1342-1363. doi:10.1002/1521- 3757(20020415)114:83.0.C O;2-A
    • (2002) Angew. Chem. , vol.114 , pp. 1342-1363
    • Herrmann, W.A.1
  • 15
    • 0037090932 scopus 로고    scopus 로고
    • doi: 10.1002/1521-3773(20020415)41:83.0.CO; 2-Y
    • Angew. Chem., Int. Ed. 2002, 41, 1290-1309. doi:10.1002/1521- 3773(20020415)41:83.0.CO; 2-Y
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1290-1309
  • 17
    • 0035807528 scopus 로고    scopus 로고
    • Enantioselective ruthenium-catalyzed ring-closing metathesis
    • DOI 10.1021/ol0165692
    • Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225-3228. doi:10.1021/ol0165692 (Pubitemid 33621155)
    • (2001) Organic Letters , vol.3 , Issue.20 , pp. 3225-3228
    • Seiders, T.J.1    Ward, D.W.2    Grubbs, R.H.3
  • 18
    • 40149107472 scopus 로고    scopus 로고
    • Enantioselective, NHC-catalyzed bicyclo-β-lactam formation via direct annulations of enals and unsaturated N-sulfonyl ketimines
    • DOI 10.1021/ja0778592
    • He, M.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 418-419. doi:10.1021/ja0778592 (Pubitemid 351455537)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.2 , pp. 418-419
    • He, M.1    Bode, J.W.2
  • 19
    • 70449362294 scopus 로고    scopus 로고
    • doi: 10.1021/ja809382c
    • Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3160-3161. doi:10.1021/ja809382c
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 3160-3161
    • Lee, Y.1    Hoveyda, A.H.2
  • 27
    • 0035906503 scopus 로고    scopus 로고
    • Improved catalysts for the palladium-catalyzed synthesis of oxindoles by amide α-arylation. Rate acceleration, use of aryl chloride substrates, and a new carbene ligand for asymmetric transformations
    • DOI 10.1021/jo005761z
    • Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402-3415. doi:10.1021/jo005761z (Pubitemid 32878948)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.10 , pp. 3402-3415
    • Lee, S.1    Hartwig, J.F.2
  • 30
    • 0037124885 scopus 로고    scopus 로고
    • doi: 10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO ;2-4
    • Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008-2022. doi:10.1002/1521-3773(20020617)41:123.0.CO ;2-4
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2008-2022
    • Noyori, R.1
  • 31
    • 0042880939 scopus 로고    scopus 로고
    • doi: 10.1021/cr020025b
    • Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155-3212. doi:10.1021/cr020025b
    • (2003) Chem. Rev. , vol.103 , pp. 3155-3212
    • Chen, Y.1    Yekta, S.2    Yudin, A.K.3
  • 32
    • 17244369977 scopus 로고    scopus 로고
    • BINOL: A versatile chiral reagent
    • DOI 10.1021/cr040079g
    • Brunel, J. M. Chem. Rev. 2005, 105, 857-898. doi:10.1021/cr040079g (Pubitemid 40527378)
    • (2005) Chemical Reviews , vol.105 , Issue.3 , pp. 857-897
    • Brunel, J.M.1
  • 34
    • 21344442252 scopus 로고    scopus 로고
    • Catalytic asymmetric olefin metathesis
    • Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany
    • Hoveyda, A. H. Catalytic Asymmetric Olefin Metathesis. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003.
    • (2003) Handbook of Metathesis
    • Hoveyda, A.H.1
  • 35
    • 1842796379 scopus 로고    scopus 로고
    • doi: 10.1002/ange.200300576
    • Schrock, R. R.; Hoveyda, A. H. Angew. Chem. 2003, 115, 4740-4782. doi:10.1002/ange.200300576
    • (2003) Angew. Chem. , vol.115 , pp. 4740-4782
    • Schrock, R.R.1    Hoveyda, A.H.2
  • 37
    • 0035793845 scopus 로고    scopus 로고
    • doi: 10.1002/1521-3765(20010302)7:5<945::AID-CHEM945>3.0.CO;2- 3
    • Hoveyda, A. H.; Schrock, R. R. Chem.-Eur. J. 2001, 7, 945-950. doi:10.1002/1521-3765(20010302)7:53.0.CO;2- 3
    • (2001) Chem.-Eur. J. , vol.7 , pp. 945-950
    • Hoveyda, A.H.1    Schrock, R.R.2
  • 38
    • 0001712693 scopus 로고    scopus 로고
    • 8<1456::AID-ANIE14 56>3.0.CO;2-T doi:10.1002/1521-3757(20010417) 113:8<1504::AID-ANGE1504>3.0.C O;2-V Angew. Chem., Int. Ed. 2001, 40, 1456-1460.doi:10.1002/1521-3773(20010417)40
    • Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem. 2001, 113, 1504-1508. doi:10.1002/1521-3757(20010417)113:83.0.C O;2-V Angew. Chem., Int. Ed. 2001, 40, 1456-1460.doi:10.1002/1521-3773(20010417)40:83. 0.CO;2-T
    • (2001) Angew. Chem. , vol.113 , pp. 1504-1508
    • Luchaco-Cullis, C.A.1    Mizutani, H.2    Murphy, K.E.3    Hoveyda, A.H.4
  • 39
    • 0037462119 scopus 로고    scopus 로고
    • Enantioselective synthesis of α-alkyl-β,γ-unsaturated esters through efficient Cu-catalyzed allylic alkylations
    • DOI 10.1021/ja0300618
    • Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4690-4691. doi:10.1021/ja0300618 (Pubitemid 36505345)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.16 , pp. 4690-4691
    • Murphy, K.E.1    Hoveyda, A.H.2
  • 40
    • 4344569716 scopus 로고    scopus 로고
    • Cu-catalyzed asymmetric allylic alkylations of aromatic and aliphatic phosphates with alkylzinc reagents. An effective method for enantioselective synthesis of tertiary and quaternary carbons
    • DOI 10.1021/ja0478779
    • Kacprzynski, M. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 10676-10681. doi:10.1021/ja0478779 (Pubitemid 39129168)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.34 , pp. 10676-10681
    • Kacprzynski, M.A.1    Hoveyda, A.H.2
  • 43
    • 33947288010 scopus 로고    scopus 로고
    • The use of chiral BINAM NHC-Rh(III) complexes in enantioselective hydrosilylation of 3-oxo-3-arylpropionic acid methyl or ethyl esters
    • DOI 10.1021/jo062453d
    • Xu, Q.; Gu, X.; Liu, S.; Dou, Q.; Shi, M. J. Org. Chem. 2007, 72, 2240-2242. doi:10.1021/jo062453d (Pubitemid 46418437)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.6 , pp. 2240-2242
    • Xu, Q.1    Gu, X.2    Liu, S.3    Dou, Q.4    Shi, M.5
  • 44
    • 49249089838 scopus 로고    scopus 로고
    • doi: 10.1002/chem.200701982
    • Zhang, T.; Shi, M. Chem.-Eur. J. 2008, 14, 3759-3764. doi:10.1002/chem.200701982
    • (2008) Chem.-Eur. J. , vol.14 , pp. 3759-3764
    • Zhang, T.1    Shi, M.2
  • 45
    • 64349110334 scopus 로고    scopus 로고
    • doi: 10.1021/ol802861s
    • Ma, G.-N.; Zhang, T.; Shi, M. Org. Lett. 2009, 11, 875-878. doi:10.1021/ol802861s
    • (2009) Org. Lett. , vol.11 , pp. 875-878
    • Ma, G.-N.1    Zhang, T.2    Shi, M.3
  • 48
    • 77953729538 scopus 로고    scopus 로고
    • doi: 10.1021/om100331z
    • Liu, Z.; Shi, M. Organometallics 2010, 29, 2831-2834. doi:10.1021/om100331z
    • (2010) Organometallics , vol.29 , pp. 2831-2834
    • Liu, Z.1    Shi, M.2
  • 52
    • 34547115739 scopus 로고    scopus 로고
    • Palladium(II) complexes containing a bulky pyridinyl N-heterocyclic carbene ligand: Preparation and reactivity
    • DOI 10.1016/j.jorganchem.2007.06.007, PII S0022328X07004147
    • Wang, C.-Y.; Liu, Y.-H.; Peng, S.-M.; Chen, J.-T.; Liu, S.-T. J. Organomet. Chem. 2007, 692, 3976-3983. doi:10.1016/j.jorganchem.2007.06.007 (Pubitemid 47101846)
    • (2007) Journal of Organometallic Chemistry , vol.692 , Issue.18 , pp. 3976-3983
    • Wang, C.-Y.1    Liu, Y.-H.2    Peng, S.-M.3    Chen, J.-T.4    Liu, S.-T.5
  • 55
    • 79955902663 scopus 로고    scopus 로고
    • 000 = 1336; Diffractometer: Bruker Smart CCD
    • 000 = 1336; Diffractometer: Bruker Smart CCD.
  • 58
    • 18844389759 scopus 로고    scopus 로고
    • Synthesis and structural characterization of N-heterocyclic carbene gold(I) complexes
    • DOI 10.1021/om050111c
    • de Frémont, P.; Scott, N. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 2411-2418. doi:10.1021/om050111c (Pubitemid 40683464)
    • (2005) Organometallics , vol.24 , Issue.10 , pp. 2411-2418
    • De Fremont, P.1    Scott, N.M.2    Stevens, E.D.3    Nolan, S.P.4
  • 59
    • 33847265371 scopus 로고    scopus 로고
    • Palladium(II) and gold(I) complexes of a new O-functionalized N-heterocyclic carbene ligand: Synthesis, structures, and catalytic application
    • DOI 10.1021/om060834b
    • Ray, L.; Shaikh, M. M.; Ghosh, P. Organometallics 2007, 26, 958-964. doi:10.1021/om060834b (Pubitemid 46326811)
    • (2007) Organometallics , vol.26 , Issue.4 , pp. 958-964
    • Ray, L.1    Shaikh, M.M.2    Ghosh, P.3
  • 60
    • 79955898757 scopus 로고    scopus 로고
    • 000 = 1376; R1 = 0.0478, wR2 = 0.1273. Diffractometer: Bruker Smart CCD
    • 000 = 1376; R1 = 0.0478, wR2 = 0.1273. Diffractometer: Bruker Smart CCD.
  • 63
    • 66149098188 scopus 로고    scopus 로고
    • doi: 10.1016/j.jorganchem.2009.03.031
    • Zhang, X.; Gu, S.; Xia, Q.; Chen, W. J. Organomet. Chem. 2009, 694, 2359-2367. doi:10.1016/j.jorganchem.2009.03.031
    • (2009) J. Organomet. Chem. , vol.694 , pp. 2359-2367
    • Zhang, X.1    Gu, S.2    Xia, Q.3    Chen, W.4
  • 65
    • 34648832247 scopus 로고    scopus 로고
    • Synthesis of benzo[c]chromen-6-ones via novel cyclic aryl-Pd(II)-ester enolate intermediates
    • DOI 10.1016/j.tet.2007.08.080, PII S0040402007015050
    • Taylor, S. R.; Ung, A. T.; Pyne, S. G. Tetrahedron 2007, 63, 10889-10895. doi:10.1016/j.tet.2007.08.080 (Pubitemid 47464429)
    • (2007) Tetrahedron , vol.63 , Issue.45 , pp. 10889-10895
    • Taylor, S.R.1    Ung, A.T.2    Pyne, S.G.3
  • 70
    • 65249085198 scopus 로고    scopus 로고
    • doi: 10.1021/jo900053b
    • Chai, D. I.; Lautens, M. J. Org. Chem. 2009, 74, 3054-3061. doi:10.1021/jo900053b
    • (2009) J. Org. Chem. , vol.74 , pp. 3054-3061
    • Chai, D.I.1    Lautens, M.2
  • 74
    • 2142705745 scopus 로고    scopus 로고
    • Cross-Coupling and Dehalogenation Reactions Catalyzed by (N-Heterocyclic carbene)Pd(allyl)Cl Complexes
    • DOI 10.1021/jo035834p
    • Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173-3180. doi:10.1021/jo035834p (Pubitemid 38542573)
    • (2004) Journal of Organic Chemistry , vol.69 , Issue.9 , pp. 3173-3180
    • Navarro, O.1    Kaur, H.2    Mahjoor, P.3    Nolan, S.P.4
  • 76
    • 50949117366 scopus 로고    scopus 로고
    • doi: 10.1039/b711132k
    • Marion, N.; Nolan, S. P. Chem. Soc. Rev. 2008, 37, 1776-1782. doi:10.1039/b711132k
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1776-1782
    • Marion, N.1    Nolan, S.P.2
  • 78
    • 18244399612 scopus 로고    scopus 로고
    • Intramolecular [4 + 2] cycloadditions of 1,3-enynes or arylalkynes with alkenes with highly reactive cationic phosphine Au(I) complexes
    • DOI 10.1021/ja042257t
    • Nieto-Oberhuber, C.; López, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178-6179. doi:10.1021/ja042257t (Pubitemid 40627735)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.17 , pp. 6178-6179
    • Nieto-Oberhuber, C.1    Lopez, S.2    Echavarren, A.M.3
  • 86
    • 48149105517 scopus 로고    scopus 로고
    • doi: 10.1002/anie.200801136
    • Angew. Chem., Int. Ed. 2008, 47, 5224-5228.doi:10.1002/anie.200801136
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 5224-5228
  • 88
    • 77952854707 scopus 로고    scopus 로고
    • doi: 10.1039/b925794m
    • van der Vlugt, J. I. Chem. Soc. Rev. 2010, 39, 2302-2322. doi:10.1039/b925794m
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 2302-2322
    • Van Der Vlugt, J.I.1
  • 90
    • 75749138175 scopus 로고    scopus 로고
    • doi: 10.1002/anie.200905341
    • Angew. Chem., Int. Ed. 2010, 49, 942-945.doi:10.1002/anie.200905341
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 942-945
  • 92
    • 78649853799 scopus 로고    scopus 로고
    • doi: 10.1002/anie.201002354
    • Angew. Chem., Int. Ed. 2011, 50, 86-95. doi:10.1002/anie.201002354
    • (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 86-95
  • 100
    • 67149095011 scopus 로고    scopus 로고
    • doi: 10.1021/ol900730w
    • Li, H.; Widenhoefer, R. A. Org. Lett. 2009, 11, 2671-2674. doi:10.1021/ol900730w
    • (2009) Org. Lett. , vol.11 , pp. 2671-2674
    • Li, H.1    Widenhoefer, R.A.2


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