Synthesis of α- and β-Carbolines by a Metalation/Negishi Cross- Coupling/SNAr Reaction Sequence

Sathiyalingam, S and Roesner, S ORCID: 0000-0003-2143-4708 (2022) Synthesis of α- and β-Carbolines by a Metalation/Negishi Cross- Coupling/SNAr Reaction Sequence. Advanced Synthesis & Catalysis, 364 (10). pp. 1769-1774. ISSN 1615-4150

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Abstract

A methodology for the synthesis of α- and β-carbolines from fluoropyridines and 2-haloanilines is reported. This procedure consists of a four-step directed ortho-lithiation, zincation, Negishi cross-coupling, and intramolecular nucleophilic aromatic substitution, providing access to a diverse set of functionalized carbolines. While the procedure is applicable to batch conditions, the generation of arylzinc intermediates in continuous flow has been demonstrated.

Item Type:	Article
Uncontrolled Keywords:	0302 Inorganic Chemistry; 0305 Organic Chemistry; 0904 Chemical Engineering; Organic Chemistry
Subjects:	Q Science > QB Astronomy Q Science > QC Physics
Divisions:	Pharmacy and Biomolecular Sciences
Publisher:	Wiley
Date of acceptance:	16 April 2022
Date of first compliant Open Access:	23 April 2024
Date Deposited:	23 Apr 2024 10:51
Last Modified:	03 Jul 2025 12:37
DOI or ID number:	10.1002/adsc.202200127
URI:	https://researchonline.ljmu.ac.uk/id/eprint/23113

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