Decarboxylative Chlorination of Coumarin-3-Carboxylic Acids Enabled by an AlCl3/Al(NO3)3 System

Vandana Thotathil; Mariam T Sayed; Arif Özturk; Ameera Al-Jabiry; Naheed Sidiq; Peter Kasák; Anas Abutaha; Raed M Al-Zoubi; Mohanad Shkoor

doi:10.1021/acs.joc.6c00386

Decarboxylative Chlorination of Coumarin-3-Carboxylic Acids Enabled by an AlCl₃/Al(NO₃)₃ System

Vandana Thotathil
, Mariam T Sayed
, Arif Özturk
, Ameera Al-Jabiry
, Naheed Sidiq
, Peter Kasák
, Anas Abutaha
, Raed M Al-Zoubi^*
, Mohanad Shkoor^*

^*Corresponding author for this work

QEERI - Materials Unit

Qatar University
Center for Advanced Materials
Hamad Medical Corporation
Jordan University of Science and Technology

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

Abstract

A decarboxylative chlorination of coumarin-3-carboxylic acids has been achieved using a combined AlCl₃/Al(NO₃)₃ system, affording 3-chlorocoumarins in 38–78% yields across a series of substrates. Experimental observations are consistent with the involvement of radical intermediates. The transformation proceeds under transition-metal-free conditions and offers a practical route to synthetically valuable 3-chlorocoumarins. Use of AlBr₃ under analogous conditions provided the corresponding 3-bromocoumarins, whereas reactions employing AlI₃ were markedly less efficient.

Original language	English
Pages (from-to)	6460-6467
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	91
Issue number	18
Early online date	Apr 2026
DOIs	https://doi.org/10.1021/acs.joc.6c00386
Publication status	Published - 8 May 2026

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title = "Decarboxylative Chlorination of Coumarin-3-Carboxylic Acids Enabled by an AlCl3/Al(NO3)3 System",

abstract = "A decarboxylative chlorination of coumarin-3-carboxylic acids has been achieved using a combined AlCl3/Al(NO3)3 system, affording 3-chlorocoumarins in 38–78\% yields across a series of substrates. Experimental observations are consistent with the involvement of radical intermediates. The transformation proceeds under transition-metal-free conditions and offers a practical route to synthetically valuable 3-chlorocoumarins. Use of AlBr3 under analogous conditions provided the corresponding 3-bromocoumarins, whereas reactions employing AlI3 were markedly less efficient.",

author = "Vandana Thotathil and \{T Sayed\}, Mariam and Arif {\"O}zturk and Ameera Al-Jabiry and Naheed Sidiq and Peter Kas{\'a}k and Anas Abutaha and \{M Al-Zoubi\}, Raed and Mohanad Shkoor",

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doi = "10.1021/acs.joc.6c00386",

language = "English",

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T1 - Decarboxylative Chlorination of Coumarin-3-Carboxylic Acids Enabled by an AlCl3/Al(NO3)3 System

AU - Thotathil, Vandana

AU - T Sayed, Mariam

AU - Özturk, Arif

AU - Al-Jabiry, Ameera

AU - Sidiq, Naheed

AU - Kasák, Peter

AU - Abutaha, Anas

AU - M Al-Zoubi, Raed

AU - Shkoor, Mohanad

PY - 2026/5/8

Y1 - 2026/5/8

N2 - A decarboxylative chlorination of coumarin-3-carboxylic acids has been achieved using a combined AlCl3/Al(NO3)3 system, affording 3-chlorocoumarins in 38–78% yields across a series of substrates. Experimental observations are consistent with the involvement of radical intermediates. The transformation proceeds under transition-metal-free conditions and offers a practical route to synthetically valuable 3-chlorocoumarins. Use of AlBr3 under analogous conditions provided the corresponding 3-bromocoumarins, whereas reactions employing AlI3 were markedly less efficient.

AB - A decarboxylative chlorination of coumarin-3-carboxylic acids has been achieved using a combined AlCl3/Al(NO3)3 system, affording 3-chlorocoumarins in 38–78% yields across a series of substrates. Experimental observations are consistent with the involvement of radical intermediates. The transformation proceeds under transition-metal-free conditions and offers a practical route to synthetically valuable 3-chlorocoumarins. Use of AlBr3 under analogous conditions provided the corresponding 3-bromocoumarins, whereas reactions employing AlI3 were markedly less efficient.

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M3 - Article

AN - SCOPUS:105038405950

SN - 0022-3263

VL - 91

SP - 6460

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Decarboxylative Chlorination of Coumarin-3-Carboxylic Acids Enabled by an AlCl₃/Al(NO₃)₃ System

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