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Catalytic sp3–sp3 Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules

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Catalytic sp3–sp3 Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules. / Abdulla, Othman; Clayton, Adam D.; Faulkner, Robert A. et al.
In: Chemistry - A European Journal, Vol. 23, No. 7, 31.01.2017, p. 1494-1497.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Abdulla, O, Clayton, AD, Faulkner, RA, Gill, DM, Rice, CR, Walton, SM & Sweeney, JB 2017, 'Catalytic sp3–sp3 Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules', Chemistry - A European Journal, vol. 23, no. 7, pp. 1494-1497. https://doi.org/10.1002/chem.201605464

APA

Abdulla, O., Clayton, A. D., Faulkner, R. A., Gill, D. M., Rice, C. R., Walton, S. M., & Sweeney, J. B. (2017). Catalytic sp3–sp3 Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules. Chemistry - A European Journal, 23(7), 1494-1497. https://doi.org/10.1002/chem.201605464

Vancouver

Abdulla O, Clayton AD, Faulkner RA, Gill DM, Rice CR, Walton SM et al. Catalytic sp3–sp3 Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules. Chemistry - A European Journal. 2017 Jan 31;23(7):1494-1497. Epub 2017 Jan 18. doi: 10.1002/chem.201605464

Author

Abdulla, Othman ; Clayton, Adam D. ; Faulkner, Robert A. et al. / Catalytic sp3–sp3 Functionalisation of Sulfonamides : Late-Stage Modification of Drug-Like Molecules. In: Chemistry - A European Journal. 2017 ; Vol. 23, No. 7. pp. 1494-1497.

Bibtex

@article{f827a62777dc48a6bcecc153346f66b8,
title = "Catalytic sp3–sp3 Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules",
abstract = "A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp3-functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd0 catalysts and base at room temperature, direct allylation was efficiently performed, yielding products that are analogues of structural motifs seen in biologically active small molecules. The reaction was performed under mild conditions and could be applied to nanomolar sigma-receptor binders, thus enabling a late-stage functionalisation and efficient expansion of drug-like chemical space.",
keywords = "catalysis, late-stage functionalisation, palladium, sigma receptor, sulfonamides",
author = "Othman Abdulla and Clayton, {Adam D.} and Faulkner, {Robert A.} and Gill, {Duncan M.} and Rice, {Craig R.} and Walton, {Scarlett M.} and Sweeney, {Joseph B.}",
year = "2017",
month = jan,
day = "31",
doi = "10.1002/chem.201605464",
language = "English",
volume = "23",
pages = "1494--1497",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "7",

}

RIS

TY - JOUR

T1 - Catalytic sp3–sp3 Functionalisation of Sulfonamides

T2 - Late-Stage Modification of Drug-Like Molecules

AU - Abdulla, Othman

AU - Clayton, Adam D.

AU - Faulkner, Robert A.

AU - Gill, Duncan M.

AU - Rice, Craig R.

AU - Walton, Scarlett M.

AU - Sweeney, Joseph B.

PY - 2017/1/31

Y1 - 2017/1/31

N2 - A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp3-functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd0 catalysts and base at room temperature, direct allylation was efficiently performed, yielding products that are analogues of structural motifs seen in biologically active small molecules. The reaction was performed under mild conditions and could be applied to nanomolar sigma-receptor binders, thus enabling a late-stage functionalisation and efficient expansion of drug-like chemical space.

AB - A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp3-functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd0 catalysts and base at room temperature, direct allylation was efficiently performed, yielding products that are analogues of structural motifs seen in biologically active small molecules. The reaction was performed under mild conditions and could be applied to nanomolar sigma-receptor binders, thus enabling a late-stage functionalisation and efficient expansion of drug-like chemical space.

KW - catalysis

KW - late-stage functionalisation

KW - palladium

KW - sigma receptor

KW - sulfonamides

U2 - 10.1002/chem.201605464

DO - 10.1002/chem.201605464

M3 - Journal article

AN - SCOPUS:85010204710

VL - 23

SP - 1494

EP - 1497

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 7

ER -