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Volumn 73, Issue 18, 2008, Pages 7096-7101

Carbonylation of aryl chlorides with oxygen nucleophiles at atmospheric pressure. Preparation of phenyl esters as acyl transfer agents and the direct preparation of alkyl esters and carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; ALKYLATION; ATMOSPHERIC CHEMISTRY; ATMOSPHERIC PRESSURE; ATMOSPHERICS; CARBON MONOXIDE; CARBONYLATION; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; CLIMATOLOGY; ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; METEOROLOGY; NONMETALS; ORGANIC ACIDS; OXYGEN; PALLADIUM;

EID: 52449124503     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800907e     Document Type: Article
Times cited : (106)

References (39)
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    • For additional studies of aryl chloride carbonylation, see
    • For additional studies of aryl chloride carbonylation, see: Lagerlund, O.; Larhed, M. J. Comb. Chem. 2006, 8, 4.
    • (2006) J. Comb. Chem , vol.8 , pp. 4
    • Lagerlund, O.1    Larhed, M.2
  • 18
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    • A few studies have been published that report formation of aryl esters using aryl bromides and iodides. For examples, see: (a) Ramesh, C, Nakamura, R, Kubota, Y, Miwa, M, Sugi, Y. Synthesis 2003, 501
    • A few studies have been published that report formation of aryl esters using aryl bromides and iodides. For examples, see: (a) Ramesh, C.; Nakamura, R.; Kubota, Y.; Miwa, M.; Sugi, Y. Synthesis 2003, 501.
  • 21
    • 52449097145 scopus 로고    scopus 로고
    • Commercially available from Nippon Chemical Co, 103099-52-1, Also see ref 9 for a convenient synthesis
    • Commercially available from Nippon Chemical Co. (103099-52-1). Also see ref 9 for a convenient synthesis.
  • 22
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    • 2 in the presence of phosphine ligands, see: (a) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177.
    • 2 in the presence of phosphine ligands, see: (a) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177.
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    • 3 prior to use and introduction the hydroscopic phenol as a solution in DMF that was predried over 3Å MS.
    • 3 prior to use and introduction the hydroscopic phenol as a solution in DMF that was predried over 3Å MS.
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    • For discussion and exceptions, see
    • For discussion and exceptions, see: Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205-3220.
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    • Kondo, T.1    Mitsudo, T.2
  • 30
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    • Recently, a direct method for the preparation of thioesters from aryl iodides via carbonylation in ionic liquids has been published: Cao, H.; McNamee, L.; Alper, H. J. Org. Chem. 2008, 73, 3530.
    • Recently, a direct method for the preparation of thioesters from aryl iodides via carbonylation in ionic liquids has been published: Cao, H.; McNamee, L.; Alper, H. J. Org. Chem. 2008, 73, 3530.
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    • These conditions contrast those of typical trans-acylation reactions, which require a large excess of alcohol in order to drive the reaction to completion. See:, 4th ed, John Wiley and Sons, Inc, New York
    • These conditions contrast those of typical trans-acylation reactions, which require a large excess of alcohol in order to drive the reaction to completion. See: March, J. Advanced Organic Chemistry, 4th ed.; John Wiley and Sons, Inc.: New York, 1992; p 397.
    • (1992) Advanced Organic Chemistry , pp. 397
    • March, J.1
  • 32
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    • Longer reaction times and higher temperatures were required for this reaction due to the greater steric demand of the secondary alcohol and its use in only stoichiometic quantities, both of which slow the rate of reaction compared to primary alcohols
    • Longer reaction times and higher temperatures were required for this reaction due to the greater steric demand of the secondary alcohol and its use in only stoichiometic quantities, both of which slow the rate of reaction compared to primary alcohols.
  • 33
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    • Under conditions identical to entry 9, Table 3, treatment of methyl 3-methoxybenzoate with N,N-dibutylamine did not lead to detectable amide, even after 24 h. This contrast highlights the greater utility of phenyl esters as acylating agents compared to alkyl esters.
    • Under conditions identical to entry 9, Table 3, treatment of methyl 3-methoxybenzoate with N,N-dibutylamine did not lead to detectable amide, even after 24 h. This contrast highlights the greater utility of phenyl esters as acylating agents compared to alkyl esters.
  • 34
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    • A group working at Solvias has reported that this method is in fact limited to use with n-butanol. See: Blaser, H-B.; Indolese, A.; Naud, F.; Nettekoven, U.; Schnyder, A. Adv. Synth. Catal. 2004, 346, 1583.
    • A group working at Solvias has reported that this method is in fact limited to use with n-butanol. See: Blaser, H-B.; Indolese, A.; Naud, F.; Nettekoven, U.; Schnyder, A. Adv. Synth. Catal. 2004, 346, 1583.
  • 35
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    • Kato has also reported a single example of the formation of a butyl ester using atmospheric CO pressure from an heteroaryl chloride. See: Kato, Y, Niiyama, K, Nemoto, T, Jona, H, Akao, A, Okada, S, Song, Z. J, Zhao, M, Tsuchiya, Y, Tomimoto, K, Mase, T. Tetrahedron 2002, 58, 3409
    • Kato has also reported a single example of the formation of a butyl ester using atmospheric CO pressure from an heteroaryl chloride. See: Kato, Y.; Niiyama, K.; Nemoto, T.; Jona, H.; Akao, A.; Okada, S.; Song, Z. J.; Zhao, M.; Tsuchiya, Y.; Tomimoto, K.; Mase, T. Tetrahedron 2002, 58, 3409.
  • 36
    • 3142712374 scopus 로고    scopus 로고
    • Various protocols have been published for heteroaryl chloride alkyoxycarbonylation, which are activated compared to aryl chlorides. In general, these reactions are all conducted at high CO pressures. For recent examples, see: a
    • Various protocols have been published for heteroaryl chloride alkyoxycarbonylation, which are activated compared to aryl chlorides. In general, these reactions are all conducted at high CO pressures. For recent examples, see: (a) Albaneze-Walker, J.; Bazaral, C.; Leavey, T.; Dormer, P. G.; Murry, J. A. Org. Lett. 2004, 6, 2097.
    • (2004) Org. Lett , vol.6 , pp. 2097
    • Albaneze-Walker, J.1    Bazaral, C.2    Leavey, T.3    Dormer, P.G.4    Murry, J.A.5
  • 38
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    • Carbon monoxide is a highly toxic gas and should only be used in a well-ventilated fume hood and with proper leak detection equipment
    • Carbon monoxide is a highly toxic gas and should only be used in a well-ventilated fume hood and with proper leak detection equipment.
  • 39
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    • Alper has also published an aryl chloride hydroxycarbonylation method using atmospheric CO pressure; however, a maximum of 29% isolated yield is reported: Grushin, V. V, Alper, H. J. Chem. Soc. Chem. Commun. 1992, 611
    • Alper has also published an aryl chloride hydroxycarbonylation method using atmospheric CO pressure; however, a maximum of 29% isolated yield is reported: Grushin, V. V.; Alper, H. J. Chem. Soc. Chem. Commun. 1992, 611.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.