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Volumn 14, Issue 18, 2008, Pages 5555-5566

Hydrogen-bond-directed catalysis: Faster, regioselective and cleaner heck arylation of electron-rich olefins in alcohols

Author keywords

Alcohols; Heck reaction; Hydrogen bonds; Palladium catalysis; Regioselectivity

Indexed keywords

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; DOPING (ADDITIVES); ETHERS; ETHYLENE; ETHYLENE GLYCOL; GLYCOLS; HYDROGEN; OLEFINS; ORGANIC COMPOUNDS; ORGANIC POLYMERS; PALLADIUM;

EID: 49449092267     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800411     Document Type: Article
Times cited : (62)

References (124)
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    • For examples of regioisomer formation, see: a F. Berthiol, H. Doucet, M. Santelli, Appl. Organomet. Chem. 2006, 20, 855;
    • For examples of regioisomer formation, see: a) F. Berthiol, H. Doucet, M. Santelli, Appl. Organomet. Chem. 2006, 20, 855;
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    • For other examples of regioselective Heck reaction of electron-rich olefins, see: a
    • For other examples of regioselective Heck reaction of electron-rich olefins, see: a) V. Calò, A. Nacci, A. Monopoli, V. Ferola, J. Org. Chem. 2007, 72, 2596;
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    • For examples of the Heck branched products leading to bioactive compounds, see: a A. Arefalk, J. Wannberg, M. Larhed, A. Hallberg, J. Org. Chem, 2006, 71, 1265;
    • For examples of the Heck branched products leading to bioactive compounds, see: a) A. Arefalk, J. Wannberg, M. Larhed, A. Hallberg, J. Org. Chem., 2006, 71, 1265;
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    • The arylation can also be performed in a DMF-water mixture: K. S. A. Vallin, M. Larhed, A. Hallberg, J. Org. Chem. 2001, 66, 4340; this paper also shows, albeit with one example, that the regioselective Heck reaction is feasible by using a mixture of DMF and MeOH.
    • The arylation can also be performed in a DMF-water mixture: K. S. A. Vallin, M. Larhed, A. Hallberg, J. Org. Chem. 2001, 66, 4340; this paper also shows, albeit with one example, that the regioselective Heck reaction is feasible by using a mixture of DMF and MeOH.
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    • For studies on the toxicity and environmental impacts of ionic liquids, see: a) A. Romero, A. Santos, J. Tojo, A. Rodriguez, J. Hazard. Mater. 2008, 151, 268;
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    • Part of this paper was presented at an AstraZeneca meeting on February 22, 2007 and at GlaxoSmithKline on April 27, 2007. Very recently, Two communication papers appeared reporting the Heck arylation of N-acyl-N-vinylamine and 1a. respectively, in 2-propanol: a Z. H. Liu, D. Xu, W. J. Tang, L. J. Xu, J. Mo, J. L. Xiao, Tetrahedron Lett. 2008, 49, 2756;
    • Part of this paper was presented at an AstraZeneca meeting on February 22, 2007 and at GlaxoSmithKline on April 27, 2007. Very recently, Two communication papers appeared reporting the Heck arylation of N-acyl-N-vinylamine and 1a. respectively, in 2-propanol: a) Z. H. Liu, D. Xu, W. J. Tang, L. J. Xu, J. Mo, J. L. Xiao, Tetrahedron Lett. 2008, 49, 2756;
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    • [18]
    • [18]
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    • The hydroxy group of a substrate could also affect selectivities in the Heck reaction by coordinating to palladium: a I. Kondolff, H. Doucet, M. Santelli, Chem. 2006, 765;
    • The hydroxy group of a substrate could also affect selectivities in the Heck reaction by coordinating to palladium: a) I. Kondolff, H. Doucet, M. Santelli, Eur. J. Org. Chem. 2006, 765;
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    • N values of 2-propanol and ethylene glycol are 0.546 and 0.790, respectively; this parameter measures largely the hydrogen-bond-donating capability of a solvent: C Reichardt. Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Wiley-VCH, Weinheim, 2003.
    • N values of 2-propanol and ethylene glycol are 0.546 and 0.790, respectively; this parameter measures largely the hydrogen-bond-donating capability of a solvent: C Reichardt. Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Wiley-VCH, Weinheim, 2003.
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    • i is the concentration of the ion, and the salt is fully ionised in the solvent.
    • i is the concentration of the ion, and the salt is fully ionised in the solvent.
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    • [35] This provides an estimate on how well the Br ions are solvated by the alcohols in comparison with the dipolar, aprotic solvents commonly used in the Heck reaction.
    • [35] This provides an estimate on how well the Br ions are solvated by the alcohols in comparison with the dipolar, aprotic solvents commonly used in the Heck reaction.
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    • [14b] which may also facilitate bromide dissociation.
    • [14b] which may also facilitate bromide dissociation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.