C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides

Lillian A. de Ceuninck van Capelle; Kimia Rahmannia; James M. Macdonald; Christopher Richardson; Michael G. Gardiner; John H. Ryan; Rasool Babaahmadi; Steven M. Wales; Christopher J.T. Hyland

doi:10.1021/acs.joc.4c02231

C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides

Lillian A. de Ceuninck van Capelle, Kimia Rahmannia, James M. Macdonald, Christopher Richardson, Michael G. Gardiner, John H. Ryan, Rasool Babaahmadi, Steven M. Wales^*, Christopher J.T. Hyland^*

^*Corresponding author for this work

Research School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A two-step formal (4 + 1) annulation-dehydration reaction offers a convenient route to C2-arylated indoles and benzofurans. This reaction exploits the bifunctional reactivity of electron-deficient benzyl chlorides with N-sulfonyl-2-aminobenzaldehydes or salicylaldehyde derivatives. The reaction tolerates both electron-withdrawing and donating groups on the substituted aldehydes, as well as variation of electron-withdrawing groups at the para position of the benzyl chloride reagent. This work also identifies interesting byproducts resulting from the self-reaction of these benzyl chlorides under basic conditions.

Original language	English
Pages (from-to)	17488-17501
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	89
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.4c02231
Publication status	Published - 6 Dec 2024

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de Ceuninck van Capelle, L. A., Rahmannia, K., Macdonald, J. M., Richardson, C., Gardiner, M. G., Ryan, J. H., Babaahmadi, R., Wales, S. M., & Hyland, C. J. T. (2024). C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides. Journal of Organic Chemistry, 89(23), 17488-17501. https://doi.org/10.1021/acs.joc.4c02231

@article{586a415163dd4c6b833b482bc2dccadd,

title = "C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides",

abstract = "A two-step formal (4 + 1) annulation-dehydration reaction offers a convenient route to C2-arylated indoles and benzofurans. This reaction exploits the bifunctional reactivity of electron-deficient benzyl chlorides with N-sulfonyl-2-aminobenzaldehydes or salicylaldehyde derivatives. The reaction tolerates both electron-withdrawing and donating groups on the substituted aldehydes, as well as variation of electron-withdrawing groups at the para position of the benzyl chloride reagent. This work also identifies interesting byproducts resulting from the self-reaction of these benzyl chlorides under basic conditions.",

author = "{de Ceuninck van Capelle}, {Lillian A.} and Kimia Rahmannia and Macdonald, {James M.} and Christopher Richardson and Gardiner, {Michael G.} and Ryan, {John H.} and Rasool Babaahmadi and Wales, {Steven M.} and Hyland, {Christopher J.T.}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = dec,

day = "6",

doi = "10.1021/acs.joc.4c02231",

language = "English",

volume = "89",

pages = "17488--17501",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

de Ceuninck van Capelle, LA, Rahmannia, K, Macdonald, JM, Richardson, C, Gardiner, MG, Ryan, JH, Babaahmadi, R, Wales, SM & Hyland, CJT 2024, 'C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides', Journal of Organic Chemistry, vol. 89, no. 23, pp. 17488-17501. https://doi.org/10.1021/acs.joc.4c02231

C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides. / de Ceuninck van Capelle, Lillian A.; Rahmannia, Kimia; Macdonald, James M. et al.
In: Journal of Organic Chemistry, Vol. 89, No. 23, 06.12.2024, p. 17488-17501.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides

AU - de Ceuninck van Capelle, Lillian A.

AU - Rahmannia, Kimia

AU - Macdonald, James M.

AU - Richardson, Christopher

AU - Gardiner, Michael G.

AU - Ryan, John H.

AU - Babaahmadi, Rasool

AU - Wales, Steven M.

AU - Hyland, Christopher J.T.

PY - 2024/12/6

Y1 - 2024/12/6

N2 - A two-step formal (4 + 1) annulation-dehydration reaction offers a convenient route to C2-arylated indoles and benzofurans. This reaction exploits the bifunctional reactivity of electron-deficient benzyl chlorides with N-sulfonyl-2-aminobenzaldehydes or salicylaldehyde derivatives. The reaction tolerates both electron-withdrawing and donating groups on the substituted aldehydes, as well as variation of electron-withdrawing groups at the para position of the benzyl chloride reagent. This work also identifies interesting byproducts resulting from the self-reaction of these benzyl chlorides under basic conditions.

AB - A two-step formal (4 + 1) annulation-dehydration reaction offers a convenient route to C2-arylated indoles and benzofurans. This reaction exploits the bifunctional reactivity of electron-deficient benzyl chlorides with N-sulfonyl-2-aminobenzaldehydes or salicylaldehyde derivatives. The reaction tolerates both electron-withdrawing and donating groups on the substituted aldehydes, as well as variation of electron-withdrawing groups at the para position of the benzyl chloride reagent. This work also identifies interesting byproducts resulting from the self-reaction of these benzyl chlorides under basic conditions.

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C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides

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