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Volumn 13, Issue 10, 2011, Pages 2564-2567

Mild Pd-catalyzed N -arylation of methanesulfonamide and related nucleophiles: Avoiding potentially genotoxic reagents and byproducts

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED HYDROCARBON; CHLORINATED HYDROCARBON; DOFETILIDE; METHANESULFONAMIDE; PALLADIUM; PHENETHYLAMINE DERIVATIVE; SULFONAMIDE;

EID: 79956125322     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200660s     Document Type: Article
Times cited : (102)

References (46)
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    • For a list of marketed drugs containing a sulfonamide, see: Smith, D. A.; Jones, R. M. Curr. Opin. Drug Discovery Dev. 2008, 11, 72-79
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    • 3 where possible due, in part, to its high molar cost when compared to several other common bases.
    • 3 where possible due, in part, to its high molar cost when compared to several other common bases.
  • 9
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    • For examples employing Cu catalysis, see
    • For examples employing Cu catalysis, see: He, H.; Wu, Y.-J. Tetrahedron Lett. 2003, 44, 3385-3386
    • (2003) Tetrahedron Lett. , vol.44 , pp. 3385-3386
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    • For examples employing Pd catalysis, see
    • For examples employing Pd catalysis, see: Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101-1104
    • (2000) Org. Lett. , vol.2 , pp. 1101-1104
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  • 19
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    • For arylation of sulfonamides via reaction with benzynes, see
    • For arylation of sulfonamides via reaction with benzynes, see: Liu, Z.; Larock, R. C. Org. Lett. 2003, 5, 4673-4675
    • (2003) Org. Lett. , vol.5 , pp. 4673-4675
    • Liu, Z.1    Larock, R.C.2
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    • 79956115226 scopus 로고    scopus 로고
    • We have verified that methanesulfonamide provides a negative result in a mini-Ames test.
    • We have verified that methanesulfonamide provides a negative result in a mini-Ames test.
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    • Reference 8a.
    • Reference 8a.
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    • Reference 8c.
    • Reference 8c.
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    • Reference 8d.
    • Reference 8d.
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    • 79956067517 scopus 로고    scopus 로고
    • Conditions very similar to these were employed in ref 9f for the coupling of larger sulfonamides with aryl sulfonates.
    • Conditions very similar to these were employed in ref 9f for the coupling of larger sulfonamides with aryl sulfonates.
  • 38
    • 33646077886 scopus 로고    scopus 로고
    • Although Bippyphos did not result in the fastest reactions, the lack of IP surrounding this ligand could make it an attractive alternative for some applications; see
    • Although Bippyphos did not result in the fastest reactions, the lack of IP surrounding this ligand could make it an attractive alternative for some applications; see: Singer, R. A.; Doré, M.; Sieser, J. E.; Berliner, M. A. Tetrahedron Lett. 2006, 47, 3727-3731
    • (2006) Tetrahedron Lett. , vol.47 , pp. 3727-3731
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    • A palladium loading of 2 mol % was used with 3 mol % of ligand.
    • A palladium loading of 2 mol % was used with 3 mol % of ligand.
  • 42
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    • We have confirmed that the use of freshly prepared catkit provides results equivalent to those obtained when each component is added separately; however, this particular mix does turn gray over days to weeks and should no longer be used once that is observed.
    • We have confirmed that the use of freshly prepared catkit provides results equivalent to those obtained when each component is added separately; however, this particular mix does turn gray over days to weeks and should no longer be used once that is observed.
  • 43
    • 79956132497 scopus 로고    scopus 로고
    • No evidence of N -(4-bromophenyl)methanesulfonamide was observed in the crude GCMS of the reaction.
    • No evidence of N -(4-bromophenyl)methanesulfonamide was observed in the crude GCMS of the reaction.
  • 44
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    • See Supporting Information for list of failed haloheterocycles.
    • See Supporting Information for list of failed haloheterocycles.
  • 46
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    • The Pd level in our isolated dofetilide was 535 ppm.
    • The Pd level in our isolated dofetilide was 535 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.