메뉴 건너뛰기




Volumn 7, Issue , 2011, Pages 1278-1287

Bromine-lithium exchange: An efficient tool in the modular construction of biaryl ligands

Author keywords

Biaryl; bromine lithium exchange; Ligand; Lithiation; Phosphine

Indexed keywords


EID: 80053033756     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.7.148     Document Type: Article
Times cited : (22)

References (75)
  • 11
    • 0037041320 scopus 로고    scopus 로고
    • Synthesis of new chiral diphosphine ligand (BisbenzodioxanPhos) and its application in asymmetric catalytic hydrogenation
    • DOI 10.1016/S0040-4039(02)00383-0, PII S0040403902003830
    • Pai, C.-C.; Li, Y.-M.; Zhou, Z.-Y.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 2789-2792. doi:10.1016/S0040-4039(02)00383-0 (Pubitemid 34261083)
    • (2002) Tetrahedron Letters , vol.43 , Issue.15 , pp. 2789-2792
    • Pai, C.-C.1    Li, Y.-M.2    Zhou, Z.-Y.3    Chan, A.S.C.4
  • 12
  • 17
    • 84942767100 scopus 로고
    • 57 - Organopalladium Compounds in Organic Synthesis and in Catalysis
    • Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, UK doi:10.1016/B978-008046518-0.00121-5
    • Trost, B. M.; Verhoeven, T. R. 57 - Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, UK, 1982; Vol. 8, pp 799-938. doi:10.1016/B978-008046518-0.00121-5
    • (1982) Comprehensive Organometallic Chemistry , vol.8 , pp. 799-938
    • Trost, B.M.1    Verhoeven, T.R.2
  • 19
    • 0001186913 scopus 로고
    • 3.4 - Transition metal alkyl complexes: Oxidative addition and transmetallation
    • Abel, E.; Stone, F. G. A.; Wilkinson, G., Eds.; Comprehensive Organometallic Chemistry II Pergamon: Oxford, UK
    • Farina, V. 3.4 - Transition Metal Alkyl Complexes: Oxidative Addition and Transmetallation. In Transition Metal Organometallics in Organic Synthesis; Abel, E.; Stone, F. G. A.; Wilkinson, G., Eds.; Comprehensive Organometallic Chemistry II, Vol. 12; Pergamon: Oxford, UK, 1995; pp 161-240.
    • (1995) Transition Metal Organometallics in Organic Synthesis , vol.12 , pp. 161-240
    • Farina, V.1
  • 21
    • 0346786657 scopus 로고    scopus 로고
    • doi:10.1016/S0022-328X(98)01055-9
    • Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. doi:10.1016/S0022- 328X(98)01055-9
    • (1999) J. Organomet. Chem. , vol.576 , pp. 147-168
    • Suzuki, A.1
  • 22
    • 2042507954 scopus 로고
    • doi:10.1021/cr00039a007
    • Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. doi:10.1021/cr00039a007
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 33
    • 12344258124 scopus 로고    scopus 로고
    • The 2 x 3 toolbox of organometallic methods for regiochemically exhaustive functionalization
    • DOI 10.1002/anie.200300645
    • Schlosser, M. Angew. Chem., Int. Ed. 2005, 44, 376-393. doi:10.1002/anie.200300645 (Pubitemid 40138340)
    • (2005) Angewandte Chemie - International Edition , vol.44 , Issue.3 , pp. 376-393
    • Schlosser, M.1
  • 34
    • 0037970037 scopus 로고    scopus 로고
    • Organoalkali chemistry
    • Schlosser M., Ed.; John Wiley and Sons: Chichester, UK
    • Schlosser, M. Organoalkali Chemistry. In Organometallic in Synthesis: A Manual, 2nd ed.; Schlosser, M., Ed.; John Wiley and Sons: Chichester, UK, 2002; pp 1-352.
    • (2002) Organometallic in Synthesis: A Manual, 2nd Ed , pp. 1-352
    • Schlosser, M.1
  • 35
    • 14844306483 scopus 로고    scopus 로고
    • The preparation of organolithium reagents and intermediates
    • Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, UK
    • Leroux, F.; Schlosser, M.; Zohar, E.; Marek, I. The preparation of organolithium reagents and intermediates. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, UK, 2004; Vol. 1, pp 435-493.
    • (2004) The Chemistry of Organolithium Compounds , vol.1 , pp. 435-493
    • Leroux, F.1    Schlosser, M.2    Zohar, E.3    Marek, I.4
  • 36
    • 0037112726 scopus 로고    scopus 로고
    • doi:10.1002/ 1521-3773 (20021115) 41:22<4272:: AID-ANIE4272>3.0.CO ;2-B
    • Leroux, F.; Schlosser, M. Angew. Chem., Int. Ed. 2002, 41, 4272-4274. doi:10.1002/1521-3773 (20021115) 41:22<4272 :: AID-ANIE4272>3.0.CO ;2-B
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4272-4274
    • Leroux, F.1    Schlosser, M.2
  • 43
  • 45
    • 0001739034 scopus 로고
    • doi:10.1021/cr60171a004
    • Jones, R. G.; Gilman, H. Chem. Rev. 1954, 54, 853-890. doi:10.1021/cr60171a004
    • (1954) Chem. Rev. , vol.54 , pp. 853-890
    • Jones, R.G.1    Gilman, H.2
  • 48
    • 85022693248 scopus 로고
    • doi:10.1021/ja00035a039
    • Beak, P.; Allen, D. J. J. Am. Chem. Soc. 1992, 114, 3420-3425. doi:10.1021/ja00035a039
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 3420-3425
    • Beak, P.1    Allen, D.J.2
  • 49
    • 0038339176 scopus 로고    scopus 로고
    • doi:10.1021/om0109408
    • Eisch, J. J. Organometallics 2002, 21, 5439-5463. doi:10.1021/om0109408
    • (2002) Organometallics , vol.21 , pp. 5439-5463
    • Eisch, J.J.1
  • 50
    • 0242352416 scopus 로고    scopus 로고
    • Recent synthetic uses of functionalised aromatic and heteroaromatic organolithium reagents prepared by non-deprotonating methods
    • DOI 10.1016/j.tet.2003.09.065
    • Nájera, C.; Sansano, J. M.; Yus, M. Tetrahedron 2003, 59, 9255-9303. doi:10.1016/j.tet.2003.09.065 (Pubitemid 37336495)
    • (2003) Tetrahedron , vol.59 , Issue.47 , pp. 9255-9303
    • Najera, C.1    Sansano, J.M.2    Yus, M.3
  • 52
    • 33645400620 scopus 로고    scopus 로고
    • doi:10.1055/s-2006-933107
    • Leroux, F.; Mettler, H. Synlett 2006, 766-770. doi:10.1055/s-2006-933107
    • (2006) Synlett , pp. 766-770
    • Leroux, F.1    Mettler, H.2
  • 57
    • 4544311534 scopus 로고    scopus 로고
    • A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides
    • DOI 10.1002/anie.200454084
    • Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333-3336. doi:10.1002/anie.200454084 (Pubitemid 39257594)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.25 , pp. 3333-3336
    • Krasovskiy, A.1    Knochel, P.2
  • 59
    • 84890994745 scopus 로고    scopus 로고
    • Polyfunctional magnesium organometallics for organic synthesis
    • Knochel, P., Ed.; Wiley-VCH: Weinheim, Germany doi:10.1002/9783527619467
    • Knochel, P.; Krasovskiy, A.; Sapountzis, I. Polyfunctional Magnesium Organometallics for Organic Synthesis. In Handbook of Functionalized Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 109-172. doi:10.1002/9783527619467
    • (2005) Handbook of Functionalized Organometallics , pp. 109-172
    • Knochel, P.1    Krasovskiy, A.2    Sapountzis, I.3
  • 60
    • 0034672069 scopus 로고    scopus 로고
    • doi:10.1002/1521-3773 (20001215) 39: 24<4414:: AID-ANIE4414>3.0.CO ;2-C
    • Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435. doi:10.1002/1521-3773(20001215)39:24<4414::AID- ANIE4414>3.0.CO ;2-C
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4414-4435
    • Boudier, A.1    Bromm, L.O.2    Lotz, M.3    Knochel, P.4
  • 61
    • 0033570284 scopus 로고    scopus 로고
    • Bromine-magnesium-exchange as a general tool for the preparation of polyfunctional aryl and heteroaryl magnesium-reagents
    • DOI 10.1016/S0040-4039(99)01404-5, PII S0040403999014045
    • Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453. doi:10.1016/S0040-4039(99)01404-5 (Pubitemid 29481188)
    • (1999) Tetrahedron Letters , vol.40 , Issue.42 , pp. 7449-7453
    • Abarbri, M.1    Dehmel, F.2    Knochel, P.3
  • 62
    • 0035898722 scopus 로고    scopus 로고
    • Tributylmagnesium ate complex-mediated novel bromine-magnesium exchange reaction for selective monosubstitution of dibromoarenes
    • DOI 10.1016/S0040-4039(01)00861-9, PII S0040403901008619
    • Iida, T.; Wada, T.; Tomimoto, K.; Mase, T. Tetrahedron Lett. 2001, 42, 4841-4844. doi:10.1016/S0040-4039(01)00861-9 (Pubitemid 32588664)
    • (2001) Tetrahedron Letters , vol.42 , Issue.29 , pp. 4841-4844
    • Iida, T.1    Wada, T.2    Tomimoto, K.3    Mase, T.4
  • 63
    • 0001253905 scopus 로고    scopus 로고
    • doi:10.1002/1521-3773 (20010601) 40:11<2085:: AID-ANIE2085>3.0.CO ;2-K
    • Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2001, 40, 2085-2087. doi:10.1002/1521-3773(20010601)40:11<2085::AID- ANIE2085>3.0.CO ;2-K
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2085-2087
    • Kondo, J.1    Inoue, A.2    Shinokubo, H.3    Oshima, K.4
  • 66
    • 0037037947 scopus 로고    scopus 로고
    • Non-cryogenic metalation of aryl bromides bearing proton donating groups: Formation of a stable magnesio-intermediate
    • DOI 10.1016/S0040-4039(02)01747-1, PII S0040403902017471
    • Kato, S.; Nonoyama, N.; Tomimoto, K.; Mase, T. Tetrahedron Lett. 2002, 43, 7315-7317. doi:10.1016/S0040-4039(02)01747-1 (Pubitemid 35287103)
    • (2002) Tetrahedron Letters , vol.43 , Issue.41 , pp. 7315-7317
    • Kato, S.1    Nonoyama, N.2    Tomimoto, K.3    Mase, T.4
  • 69
    • 78349299724 scopus 로고    scopus 로고
    • doi:10.1002/adsc.201000517
    • Perron, Q.; Alexakis, A. Adv. Synth. Catal. 2010, 352, 2611-2620. doi:10.1002/adsc.201000517
    • (2010) Adv. Synth. Catal. , vol.352 , pp. 2611-2620
    • Perron, Q.1    Alexakis, A.2
  • 74
    • 80053030529 scopus 로고    scopus 로고
    • CCDC 827188 (3a), CCDC 827186 (3b), CCDC 827187 (3d), CCDC 827189 (3f) and CCDC 827190 (6c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 827188 (3a), CCDC 827186 (3b), CCDC 827187 (3d), CCDC 827189 (3f) and CCDC 827190 (6c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data-request/cif.
  • 75


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.