Nickel-catalyzed cross-coupling reaction of alkynyl bromides with Grignard reagents
English
Nickel-catalyzed cross-coupling reaction of alkynyl bromides with Grignard reagents
-
Key words:
- 1,2-Disubstituted acetylene
- / Nickel
- / (Bromoethynyl)benzene
- / Grignard reagent
- / Cross-coupling
-
-
-
[1] J.B. Johnson, T. Rovis, More than bystanders: the effect of olefins on transitionmetal-catalyzed cross-coupling reactions, Angew. Chem. Int. Ed. 47 (2008) 840-871.[1] J.B. Johnson, T. Rovis, More than bystanders: the effect of olefins on transitionmetal-catalyzed cross-coupling reactions, Angew. Chem. Int. Ed. 47 (2008) 840-871.
-
[2] D.G. Yu, Z.J. Shi, Mutual activation: Suzuki-Miyaura coupling through direct cleavage of the sp2 C-O bond of naphtholate, Angew. Chem. Int. Ed. 50 (2011) 7079-7100.[2] D.G. Yu, Z.J. Shi, Mutual activation: Suzuki-Miyaura coupling through direct cleavage of the sp2 C-O bond of naphtholate, Angew. Chem. Int. Ed. 50 (2011) 7079-7100.
-
[3] J.J. Hirner, S.A. Blum, Nickel-catalyzed cross-coupling of organogold reagents, Organometallics 30 (2011) 1299-1302.[3] J.J. Hirner, S.A. Blum, Nickel-catalyzed cross-coupling of organogold reagents, Organometallics 30 (2011) 1299-1302.
-
[4] M.A. Greene, I.M. Yonova, F.J. Williams, E.R. Jarvo, Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions, Org. Lett. 14 (2012) 4293-4296.[4] M.A. Greene, I.M. Yonova, F.J. Williams, E.R. Jarvo, Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions, Org. Lett. 14 (2012) 4293-4296.
-
[5] X.Q. Zhang, Z.X. Wang, Amido pincer nickel catalyzed Kumada cross-coupling of aryl, heteroaryl, and vinyl chlorides, Synlett 24 (2013) 2081-2084.[5] X.Q. Zhang, Z.X. Wang, Amido pincer nickel catalyzed Kumada cross-coupling of aryl, heteroaryl, and vinyl chlorides, Synlett 24 (2013) 2081-2084.
-
[6] D.A. Everson, J.A. Buonomo, D.J. Weix, Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides, Synlett 25 (2014) 233-238.[6] D.A. Everson, J.A. Buonomo, D.J. Weix, Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides, Synlett 25 (2014) 233-238.
-
[7] K. Sonogashira, Y. Tohda, N. Hagihara, A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines, Tetrahedron Lett. 50 (1975) 4467-4470.[7] K. Sonogashira, Y. Tohda, N. Hagihara, A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines, Tetrahedron Lett. 50 (1975) 4467-4470.
-
[8] R. Chinchilla, C. Nájera, The Sonogashira reaction: a booming methodology in synthetic organic chemistry, Chem. Rev. 107 (2007) 874-922.[8] R. Chinchilla, C. Nájera, The Sonogashira reaction: a booming methodology in synthetic organic chemistry, Chem. Rev. 107 (2007) 874-922.
-
[9] E.M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents, Chem. Rev. 107 (2007) 5318-5365.[9] E.M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents, Chem. Rev. 107 (2007) 5318-5365.
-
[10] D. Doucet, J.C. Hierso, Palladium-based catalytic systems for the synthesis of conjugated enynes by Sonogashira reactions and related alkynylations, Angew. Chem. Int. Ed. 46 (2007) 834-871.[10] D. Doucet, J.C. Hierso, Palladium-based catalytic systems for the synthesis of conjugated enynes by Sonogashira reactions and related alkynylations, Angew. Chem. Int. Ed. 46 (2007) 834-871.
-
[11] H. Plenio, Catalysts for the Sonogashira coupling -the crownless again shall be king, Angew. Chem. Int. Ed. 47 (2008) 6954-6956.[11] H. Plenio, Catalysts for the Sonogashira coupling -the crownless again shall be king, Angew. Chem. Int. Ed. 47 (2008) 6954-6956.
-
[12] M.M. Heravi, S. Sadjadi, Recent advances in the application of the Sonogashira method in the synthesis of heterocyclic compounds, Tetrahedron 65 (2009) 7761-7775.[12] M.M. Heravi, S. Sadjadi, Recent advances in the application of the Sonogashira method in the synthesis of heterocyclic compounds, Tetrahedron 65 (2009) 7761-7775.
-
[13] K.C. Nicolaou, W.M. Dai, Chemistry and biology of the enediyne anticancer antibiotics, Angew. Chem. Int. Ed. 30 (1991) 1387-1416.[13] K.C. Nicolaou, W.M. Dai, Chemistry and biology of the enediyne anticancer antibiotics, Angew. Chem. Int. Ed. 30 (1991) 1387-1416.
-
[14] J.W. Grissom, G.U. Gunawardena, D. Klingberg, D.H. Huang, The chemistry of enediynes, enyne allenes and related compounds, Tetrahedron 52 (1996) 6453-6518.[14] J.W. Grissom, G.U. Gunawardena, D. Klingberg, D.H. Huang, The chemistry of enediynes, enyne allenes and related compounds, Tetrahedron 52 (1996) 6453-6518.
-
[15] T. Haro, C. Nevado, Gold-catalyzed ethynylation of arenes, J. Am. Chem. Soc. 132 (2010) 1512-1513.[15] T. Haro, C. Nevado, Gold-catalyzed ethynylation of arenes, J. Am. Chem. Soc. 132 (2010) 1512-1513.
-
[16] B. Panda, T.K. Sarkar, On the catalytic duo PdCl2(PPh3)2/AuCl(PPh3) that cannot effect a Sonogashira-type reaction: a correction, Tetrahedron Lett. 51 (2010) 301-305.[16] B. Panda, T.K. Sarkar, On the catalytic duo PdCl2(PPh3)2/AuCl(PPh3) that cannot effect a Sonogashira-type reaction: a correction, Tetrahedron Lett. 51 (2010) 301-305.
-
[17] M. Carril, A. Correa, C. Bolm, Iron-catalyzed Sonogashira reactions, Angew. Chem. Int. Ed. 47 (2008) 4862-4865.[17] M. Carril, A. Correa, C. Bolm, Iron-catalyzed Sonogashira reactions, Angew. Chem. Int. Ed. 47 (2008) 4862-4865.
-
[18] L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse, Application of Transition Metal Catalysts in Organic Synthesis, Springer-Verlag, Berlin, 1988, pp. 179-225.[18] L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse, Application of Transition Metal Catalysts in Organic Synthesis, Springer-Verlag, Berlin, 1988, pp. 179-225.
-
[19] K.C. Nicolau, E.J. Sorensen, Classics in Total Synthesis, Wiley-VCH, Weinheim, 1996, pp. 582-586.[19] K.C. Nicolau, E.J. Sorensen, Classics in Total Synthesis, Wiley-VCH, Weinheim, 1996, pp. 582-586.
-
[20] U.H.F. Bunz, Poly(aryleneethynylene)s: syntheses, properties, structures, and applications, Chem. Rev. 100 (2000) 1605-1644.[20] U.H.F. Bunz, Poly(aryleneethynylene)s: syntheses, properties, structures, and applications, Chem. Rev. 100 (2000) 1605-1644.
-
[21] L.M. Tan, Z.Y. Sem, W.Y. Chong, et al., Continuous flow Sonogashira C-C coupling using a heterogeneous palladium-copper dual reactor, Org. Lett. 15 (2013) 65-67.[21] L.M. Tan, Z.Y. Sem, W.Y. Chong, et al., Continuous flow Sonogashira C-C coupling using a heterogeneous palladium-copper dual reactor, Org. Lett. 15 (2013) 65-67.
-
[22] R. Ciriminna, V. Pandarus, G. Gingras, et al., Heterogeneous Sonogashira coupling over nanostructured SiliaCat Pd(0), ACS Sustainable Chem. Eng. 1 (2013) 57-61.[22] R. Ciriminna, V. Pandarus, G. Gingras, et al., Heterogeneous Sonogashira coupling over nanostructured SiliaCat Pd(0), ACS Sustainable Chem. Eng. 1 (2013) 57-61.
-
[23] D.S. Yang, B. Li, H.J. Yang, H. Fu, L.I. Hu, Efficient copper-catalyzed Sonogashira couplings of aryl halides with terminal alkynes in water, Synlett 5 (2011) 702-706.[23] D.S. Yang, B. Li, H.J. Yang, H. Fu, L.I. Hu, Efficient copper-catalyzed Sonogashira couplings of aryl halides with terminal alkynes in water, Synlett 5 (2011) 702-706.
-
[24] T. Suzuka, Y. Okada, K. Ooshiro, Y. Uozumi, Copper-free Sonogashira coupling in water with an amphiphilic resin-supported palladium complex, Tetrahedron 66 (2010) 1064-1069.[24] T. Suzuka, Y. Okada, K. Ooshiro, Y. Uozumi, Copper-free Sonogashira coupling in water with an amphiphilic resin-supported palladium complex, Tetrahedron 66 (2010) 1064-1069.
-
[25] R. Severin, J. Reimer, S. Doye, One-pot procedure for the synthesis of unsymmetrical diarylalkynes, J. Org. Chem. 75 (2010) 3518-3521.[25] R. Severin, J. Reimer, S. Doye, One-pot procedure for the synthesis of unsymmetrical diarylalkynes, J. Org. Chem. 75 (2010) 3518-3521.
-
[26] Y.S. Feng, Z.Q. Xu, L. Mao, F.F. Zhang, H.J. Xu, Copper catalyzed decarboxylative alkynylation of quaternary α-cyano acetate salts, Org. Lett. 15 (2013) 1472-1475.[26] Y.S. Feng, Z.Q. Xu, L. Mao, F.F. Zhang, H.J. Xu, Copper catalyzed decarboxylative alkynylation of quaternary α-cyano acetate salts, Org. Lett. 15 (2013) 1472-1475.
-
[27] S.H. Wang, L. Yu, P.H. Li, L.G. Meng, L. Wang, Copper(I) iodide catalyzed crosscoupling reaction of terminal alkynes with 1-bromoalkynes: a simple synthesis of unsymmetrical buta-1,3-diynes, Synthesis 10 (2011) 1541-1546.[27] S.H. Wang, L. Yu, P.H. Li, L.G. Meng, L. Wang, Copper(I) iodide catalyzed crosscoupling reaction of terminal alkynes with 1-bromoalkynes: a simple synthesis of unsymmetrical buta-1,3-diynes, Synthesis 10 (2011) 1541-1546.
-
[28] K. Tsuyoshi, M. Nato, H. Koji, S. Tetsuya, M. Masahiro, Room temperature direct alkynylation of 1,3,4-oxadiazoles with alkynyl bromides under copper catalysis, J. Org. Chem. 75 (2010) 1764-1766.[28] K. Tsuyoshi, M. Nato, H. Koji, S. Tetsuya, M. Masahiro, Room temperature direct alkynylation of 1,3,4-oxadiazoles with alkynyl bromides under copper catalysis, J. Org. Chem. 75 (2010) 1764-1766.
-
[29] M. Nato, H. Koji, S. Tetsuya, M. Masahiro, Nickel-catalyzed direct alkynylation of azoles with alkynyl bromides, Org. Lett. 11 (2009) 4156-4159.[29] M. Nato, H. Koji, S. Tetsuya, M. Masahiro, Nickel-catalyzed direct alkynylation of azoles with alkynyl bromides, Org. Lett. 11 (2009) 4156-4159.
-
[30] J. Breitenfeld, J. Ruiz, M.D. Wodrich, X.L. Hu, Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl-alkyl Kumada coupling reactions, J. Am. Chem. Soc. 135 (2013) 12004-12012.[30] J. Breitenfeld, J. Ruiz, M.D. Wodrich, X.L. Hu, Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl-alkyl Kumada coupling reactions, J. Am. Chem. Soc. 135 (2013) 12004-12012.
-
[31] Q.H. Li, H.M. Gau, Synthesis of allenes via nickel-catalyzed cross-coupling reaction of propargylic bromide with Grignard reagent, Synlett 23 (2012) 747-750.[31] Q.H. Li, H.M. Gau, Synthesis of allenes via nickel-catalyzed cross-coupling reaction of propargylic bromide with Grignard reagent, Synlett 23 (2012) 747-750.
-
[32] A.M. Lauer, F. Mahmud, J.M. Wu, Cu(I)-catalyzed, α-selective, allylic alkylation reactions between phosphorothioate esters and organomagnesium reagents, J. Am. Chem. Soc. 133 (2011) 9119-9123.[32] A.M. Lauer, F. Mahmud, J.M. Wu, Cu(I)-catalyzed, α-selective, allylic alkylation reactions between phosphorothioate esters and organomagnesium reagents, J. Am. Chem. Soc. 133 (2011) 9119-9123.
-
[33] G. Cahiez, O. Gager, J. Buendia, Copper-catalyzed cross-coupling of alkyl and aryl Grignard reagents with alkynyl halides, Angew. Chem. Int. Ed. 49 (2010) 1278-1281.[33] G. Cahiez, O. Gager, J. Buendia, Copper-catalyzed cross-coupling of alkyl and aryl Grignard reagents with alkynyl halides, Angew. Chem. Int. Ed. 49 (2010) 1278-1281.
-
[34] D. Castagnolo, M. Botta, Iron-Catalyzed Cross-Coupling between 1-Bromoalkynes and Grignard-Derived Organocuprate Reagents, Eur. J.Org.Chem. 17 (2010) 3224-3228.[34] D. Castagnolo, M. Botta, Iron-Catalyzed Cross-Coupling between 1-Bromoalkynes and Grignard-Derived Organocuprate Reagents, Eur. J.Org.Chem. 17 (2010) 3224-3228.
-
[35] H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, A novel entry to 17a-bromoand 17a-iodoethynyl steroids, Angew. Chem. Int. Ed. Engl. 23 (1984) 727-729.[35] H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, A novel entry to 17a-bromoand 17a-iodoethynyl steroids, Angew. Chem. Int. Ed. Engl. 23 (1984) 727-729.
-
[36] A.D. Finke, E.C. Elleby, M.J. Boyd, H. Weissman, J.S. Moore, Zinc chloride-promoted aryl bromide-alkyne cross-coupling reactions at room temperature, J. Org. Chem. 74 (2009) 8897-8900.[36] A.D. Finke, E.C. Elleby, M.J. Boyd, H. Weissman, J.S. Moore, Zinc chloride-promoted aryl bromide-alkyne cross-coupling reactions at room temperature, J. Org. Chem. 74 (2009) 8897-8900.
-
[37] J. Moon, M. Jeong, H. Nam, et al., One-pot synthesis of diarylalkynes using palladium-catalyzed Sonogashira reaction and decarboxylative coupling of sp carbon and sp2 carbon, Org. Lett. 10 (2008) 945-948.[37] J. Moon, M. Jeong, H. Nam, et al., One-pot synthesis of diarylalkynes using palladium-catalyzed Sonogashira reaction and decarboxylative coupling of sp carbon and sp2 carbon, Org. Lett. 10 (2008) 945-948.
-
[38] X.F. Wu, H. Neumann, M. Beller, Palladium-catalyzed Sonogashira reactions of aryl amines with alkynes via in situ formation of arenediazonium salts, Chem. Commun. 47 (2011) 7959-7961.[38] X.F. Wu, H. Neumann, M. Beller, Palladium-catalyzed Sonogashira reactions of aryl amines with alkynes via in situ formation of arenediazonium salts, Chem. Commun. 47 (2011) 7959-7961.
-
-
扫一扫看文章
计量
- PDF下载量: 0
- 文章访问数: 1719
- HTML全文浏览量: 54

下载: