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Volumn 25, Issue 15, 2006, Pages 3562-3564

A highly regioselective cyanothiolation of alkynes via oxidative addition of thiocyanates to tetrakis(triphenylphosphine)palladium(0) catalyst

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; NITROGEN COMPOUNDS; OXIDATION; PALLADIUM; STEREOCHEMISTRY;

EID: 33746340891     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0600442     Document Type: Article
Times cited : (111)

References (69)
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    • See Supporting Information (method A)
    • See Supporting Information (method A).
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    • note
    • 3) δ 26.2.
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    • note
    • 2[I > 3σ(I)] = 0.049 with GOF = 1.017. The structure was solved by direct methods using SIR92 and refined by full-matrix least squares on F. Drawings were generated using ORTEP-III (Burnett & Johnson, 1996). Selected bond lengths (A): Pd(1)-S(1) 2.338-(1), Pd(1)-C(43) 1.980(4), Pd(1)-P(1) 2.339(1), Pd(1)-P(2) 2.327(1); angles (deg): P(1)-Pd(1)-S(1) 92.49(5), P(2)-Pd(1)-S(1) 84.38(5), P(1)-Pd(1)-C(2) 88.0(2), P(2)-Pd(1)-C(2) 95.0(2), P(1)-Pd(1)-P(2) 176.32-(4), S(1)-Pd(1)-C(2) 178.5(1).
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    • note
    • Atempted stoichiometric reaction of complex A with 1-octyne did not proceed. This fact suggests that the reductive elimination step may be the rate-determining step, because the presence of excess amounts of PhSCN in this reaction of complex A with 1-octyne affords the corresponding cyanothiolation products.


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