
Palladium-catalyzed ortho-selective C-H bond chlorination of aromatic ketones
English
Palladium-catalyzed ortho-selective C-H bond chlorination of aromatic ketones
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Key words:
- Palladium catalysis
- / C-H chlorination
- / Aromatic ketones
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[1] (a) A.Y. Solovyev, D.A. Androsov, D.C. Neckers, One-pot synthesis of substituted 2-aminobenzo[b]thiophenes, J. Org. Chem. 72(2007) 3122-3124;[1] (a) A.Y. Solovyev, D.A. Androsov, D.C. Neckers, One-pot synthesis of substituted 2-aminobenzo[b]thiophenes, J. Org. Chem. 72(2007) 3122-3124;
-
[2]
(b) Q. Cai, Z.Q. Li, J.J. Wei, et al., Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process, Chem. Commun. (2009) 7581-7583;(b) Q. Cai, Z.Q. Li, J.J. Wei, et al., Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process, Chem. Commun. (2009) 7581-7583;
-
[3]
(c) L.B. Fu, X.L. Huang, D.P. Wang, P.H. Zhao, K. Ding, Copper(I) iodide catalyzed synthesis of quinolinones via cascade reactions of 2-halobenzocarbonyls with 2-arylacetamides, Synthesis 10(2011) 1547-1554;(c) L.B. Fu, X.L. Huang, D.P. Wang, P.H. Zhao, K. Ding, Copper(I) iodide catalyzed synthesis of quinolinones via cascade reactions of 2-halobenzocarbonyls with 2-arylacetamides, Synthesis 10(2011) 1547-1554;
-
[4]
(d) K. Inamoto, M. Katsuno, T. Yoshino, et al., Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions:application to the synthesis of nigellicine, Tetrahedron 63(2007) 2695-2711.(d) K. Inamoto, M. Katsuno, T. Yoshino, et al., Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions:application to the synthesis of nigellicine, Tetrahedron 63(2007) 2695-2711.
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[2] K. Naumann, Influence of chlorine substituents on biological activity of chemicals:a review, Pest Manag. Sci. 56(2000) 3-21.[2] K. Naumann, Influence of chlorine substituents on biological activity of chemicals:a review, Pest Manag. Sci. 56(2000) 3-21.
-
[3] (a) R. Parella, A. Kumar Naveen, S.A. Babu, Catalytic Friedel-Crafts acylation:magnetic nanopowder CuFe2O4 as an efficient and magnetically separable catalyst, Tetrahedron Lett. 54(2013) 1738-1742;[3] (a) R. Parella, A. Kumar Naveen, S.A. Babu, Catalytic Friedel-Crafts acylation:magnetic nanopowder CuFe2O4 as an efficient and magnetically separable catalyst, Tetrahedron Lett. 54(2013) 1738-1742;
-
[7]
(b) E. Berliner, The influence of n-alkyl groups on the rate of a cyclization reaction, J. Am. Chem. Soc. 66(1944) 533-535;(b) E. Berliner, The influence of n-alkyl groups on the rate of a cyclization reaction, J. Am. Chem. Soc. 66(1944) 533-535;
-
[8]
(c) A.P. Huang, X.Y. Liu, L.H. Li, et al., Antimony(V) chloride-benzyltriethylammonium chloride complex as an efficient catalyst for Friedel-Crafts acylation reactions, Adv. Synth. Catal. 346(2004) 599-602;(c) A.P. Huang, X.Y. Liu, L.H. Li, et al., Antimony(V) chloride-benzyltriethylammonium chloride complex as an efficient catalyst for Friedel-Crafts acylation reactions, Adv. Synth. Catal. 346(2004) 599-602;
-
[9]
(d) M.S. Gowda, S.S. Pande, R.A. Ramakrishna, K.R. Prabhu, Acylation of Grignard reagents mediated by N-methylpyrrolidone:a remarkable selectivity for the synthesis of ketones, Org. Biomol. Chem. 9(2011) 5365-5368;(d) M.S. Gowda, S.S. Pande, R.A. Ramakrishna, K.R. Prabhu, Acylation of Grignard reagents mediated by N-methylpyrrolidone:a remarkable selectivity for the synthesis of ketones, Org. Biomol. Chem. 9(2011) 5365-5368;
-
[10]
(e) C. Hyun-Hee, K. Seung-Hoi, A versatile protocol for the preparation of highly hindered aryl ketones using organozinc reagents, Bull. Korean Chem. Soc. 33(2012) 3083-3086.(e) C. Hyun-Hee, K. Seung-Hoi, A versatile protocol for the preparation of highly hindered aryl ketones using organozinc reagents, Bull. Korean Chem. Soc. 33(2012) 3083-3086.
-
[4] (a) W. Zeng, T.E. Ballard, A.G. Tkachenko, et al., Mimicking the biological activity of diazobenzo[b]fluorene natural products with electronically tuned diazofluorene analogs, Bioorg. Med. Chem. Lett. 16(2006) 5148-5151;[4] (a) W. Zeng, T.E. Ballard, A.G. Tkachenko, et al., Mimicking the biological activity of diazobenzo[b]fluorene natural products with electronically tuned diazofluorene analogs, Bioorg. Med. Chem. Lett. 16(2006) 5148-5151;
-
[12]
(b) I.D. Ivanchikova, N.I. Lebedev, M.S. Shvartsberg, A simple synthesis of angular anthrathiophenediones via acetylenic derivatives of anthraquinone, Synthesis 13(2004) 2131-2134;(b) I.D. Ivanchikova, N.I. Lebedev, M.S. Shvartsberg, A simple synthesis of angular anthrathiophenediones via acetylenic derivatives of anthraquinone, Synthesis 13(2004) 2131-2134;
-
[13]
(c) C.H. Park, D.R. Brittelli, C.L. Wang, F.D. Marsh, W.A. Gregory, M.A. Wuonola, R.J. McRipley, V.S. Eberly, A.M. Slee, M. Forbes, Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 4. Multiply-substituted aryl derivatives, J. Med. Chem. 35(1992) 1156-1165.(c) C.H. Park, D.R. Brittelli, C.L. Wang, F.D. Marsh, W.A. Gregory, M.A. Wuonola, R.J. McRipley, V.S. Eberly, A.M. Slee, M. Forbes, Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 4. Multiply-substituted aryl derivatives, J. Med. Chem. 35(1992) 1156-1165.
-
[5] (a) D. Kalyani, A.R. Dick, W.Q. Anani, M.S. Sanford, A simple catalytic method for the regioselective halogenation of arenes, Org. Lett. 8(2006) 2523-2526;[5] (a) D. Kalyani, A.R. Dick, W.Q. Anani, M.S. Sanford, A simple catalytic method for the regioselective halogenation of arenes, Org. Lett. 8(2006) 2523-2526;
-
[15]
(b) C. Lu, S.Y. Zhang, G. He, W.A. Nack, G. Chen, Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates, Tetrahedron 70(2014) 4197-4203;(b) C. Lu, S.Y. Zhang, G. He, W.A. Nack, G. Chen, Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates, Tetrahedron 70(2014) 4197-4203;
-
[16]
(c) X.Y. Sun, Y.H. Sun, Y. Rao, A gram-scale synthesis of multi-substituted arenes via palladium catalyzed C-H halogenation, Chin. Chem. Lett. 25(2014) 667-669;(c) X.Y. Sun, Y.H. Sun, Y. Rao, A gram-scale synthesis of multi-substituted arenes via palladium catalyzed C-H halogenation, Chin. Chem. Lett. 25(2014) 667-669;
-
[17]
(d) B.C. Chary, S. Kim, Rhodium(III)-catalyzed ortho-olefination of aryl phosphonates, Org. Biomol. Chem. 11(2013) 6879-6882;(d) B.C. Chary, S. Kim, Rhodium(III)-catalyzed ortho-olefination of aryl phosphonates, Org. Biomol. Chem. 11(2013) 6879-6882;
-
[18]
(e) N. Schröder, J. Wencel-Delord, F. Glorius, High-yielding, versatile, and practical[Rh(III)Cp*]-catalyzed ortho-bromination and iodination of arenes, J. Am. Chem. Soc. 134(2012) 8298-8301;(e) N. Schröder, J. Wencel-Delord, F. Glorius, High-yielding, versatile, and practical[Rh(III)Cp*]-catalyzed ortho-bromination and iodination of arenes, J. Am. Chem. Soc. 134(2012) 8298-8301;
-
[19]
(f) G. Shan, X. Yang, L. Ma, Y. Rao, Pd-catalyzed C-H oxygenation with TFA/TFAA:expedient access to oxygen-containing heterocycles and late-stage drug modification, Angew. Chem. Int. Ed. 51(2012) 13070-13074.(f) G. Shan, X. Yang, L. Ma, Y. Rao, Pd-catalyzed C-H oxygenation with TFA/TFAA:expedient access to oxygen-containing heterocycles and late-stage drug modification, Angew. Chem. Int. Ed. 51(2012) 13070-13074.
-
[6] (a) X.Y. Sun, G. Shan, Y.H. Sun, Y. Rao, Regio- and chemoselective C-H chorination/bromination of electron deficient arenes by weak coordination and study of relative directing-group abilities, Angew. Chem. Int. Ed. 52(2013) 4440-4444;[6] (a) X.Y. Sun, G. Shan, Y.H. Sun, Y. Rao, Regio- and chemoselective C-H chorination/bromination of electron deficient arenes by weak coordination and study of relative directing-group abilities, Angew. Chem. Int. Ed. 52(2013) 4440-4444;
-
[21]
(b) X.Y. Sun, Y.H. Sun, C. Zhang, Y. Rao, Room-temperature Pd-catalyzed C-H chlorination by weak coordination:one-pot synthesis of 2-chlorophenols with excellent regioselectivity, Chem. Commun. 50(2014) 1262-1264.(b) X.Y. Sun, Y.H. Sun, C. Zhang, Y. Rao, Room-temperature Pd-catalyzed C-H chlorination by weak coordination:one-pot synthesis of 2-chlorophenols with excellent regioselectivity, Chem. Commun. 50(2014) 1262-1264.
-
[7] (a) K.M. Engle, T.S. Mei, M. Wasa, J.Q. Yu, Weak coordination as powerful means for developing broadly useful C-H functionalization reactions, Acc. Chem. Res. 45(2012) 788-802;[7] (a) K.M. Engle, T.S. Mei, M. Wasa, J.Q. Yu, Weak coordination as powerful means for developing broadly useful C-H functionalization reactions, Acc. Chem. Res. 45(2012) 788-802;
-
[23]
(b) T.S. Mei, R. Giri, N. Maugel, J.Q. Yu, Pd-catalyzed mono-selective orthohalogenation of C-H bonds assisted by counter cations:an orthogonal method to directed ortho-lithiation, Angew. Chem. Int. Ed. 47(2008) 5215-5219;(b) T.S. Mei, R. Giri, N. Maugel, J.Q. Yu, Pd-catalyzed mono-selective orthohalogenation of C-H bonds assisted by counter cations:an orthogonal method to directed ortho-lithiation, Angew. Chem. Int. Ed. 47(2008) 5215-5219;
-
[24]
(c) Q.Z. Zheng, N. Jiao, Transition-metal-catalyzed ketone-directed ortho-C-H functionalization reactions, Tetrahedron Lett. 55(2014) 1121-1126;(c) Q.Z. Zheng, N. Jiao, Transition-metal-catalyzed ketone-directed ortho-C-H functionalization reactions, Tetrahedron Lett. 55(2014) 1121-1126;
-
[25]
(d) L.H. Wang, L. Ackermann, Ruthenium-catalyzed ortho-C-H halogenations of benzamides, Chem. Commun. 55(2014) 1083-1085;(d) L.H. Wang, L. Ackermann, Ruthenium-catalyzed ortho-C-H halogenations of benzamides, Chem. Commun. 55(2014) 1083-1085;
-
[26]
(e) S. Ma, G. Villa, P.S. Thuy-Boun, A. Homa, J.Q. Yu, Pd-catalyzed ortho-selective C-H deuteration of arenes, evidence for superior reactivity of weakly coordinated palladacycles, Angew. Chem. Int. Ed. 53(2014) 734-737.(e) S. Ma, G. Villa, P.S. Thuy-Boun, A. Homa, J.Q. Yu, Pd-catalyzed ortho-selective C-H deuteration of arenes, evidence for superior reactivity of weakly coordinated palladacycles, Angew. Chem. Int. Ed. 53(2014) 734-737.
-
[8] B.M. Bhawal, D.S. Mukadam, K.A. Thakar, Pesticidal activity of some 1,2-benzisoxazole derivatives, Marathwada Univ. J. Sci. Nat. Sci. 17(1978) 21-22.[8] B.M. Bhawal, D.S. Mukadam, K.A. Thakar, Pesticidal activity of some 1,2-benzisoxazole derivatives, Marathwada Univ. J. Sci. Nat. Sci. 17(1978) 21-22.
-
[9] (a) X. Wang, S.X. Wang, Y.T. Liu, et al., Comparative effects of SNX-7081 and SNX-2112 on cell cycle, apoptosis and Hsp90 client proteins in human cancer cells, Oncol. Rep. 33(2015) 230-238;[9] (a) X. Wang, S.X. Wang, Y.T. Liu, et al., Comparative effects of SNX-7081 and SNX-2112 on cell cycle, apoptosis and Hsp90 client proteins in human cancer cells, Oncol. Rep. 33(2015) 230-238;
-
[29]
(b) S. Moon, M. Hanif, M. Kubanik, et al., organoruthenium and osmium anticancer complexes bearing a maleimide functional group:reactivity to cysteine, stability, and cytotoxicity, ChemPlusChem 80(2015) 231-236.(b) S. Moon, M. Hanif, M. Kubanik, et al., organoruthenium and osmium anticancer complexes bearing a maleimide functional group:reactivity to cysteine, stability, and cytotoxicity, ChemPlusChem 80(2015) 231-236.
-
[10] Y. Xia, F.D. Hu, Z.X. Liu, et al., Palladium-catalyzed diarylmethyl C(sp3)-C(sp2) bond formation:a new coupling approach toward triarylmethanes, Org. Lett. 15(2013) 1784-1787.[10] Y. Xia, F.D. Hu, Z.X. Liu, et al., Palladium-catalyzed diarylmethyl C(sp3)-C(sp2) bond formation:a new coupling approach toward triarylmethanes, Org. Lett. 15(2013) 1784-1787.
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