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Synlett
DOI: 10.1055/a-2624-9146
letter

Insights into the Heck-Type Arylation of 1,2-Dihydropyridines: Site- and Regioselective Access to 2,3-Disubstituted Dihydropyridines

Hao Ding
1   Institute of Chemistry, Casali Center of Applied Chemistry, The Hebrew University of Jerusalem, Jerusalem, Israel (Ringgold ID: RIN26742)
,
Haining Li
1   Institute of Chemistry, Casali Center of Applied Chemistry, The Hebrew University of Jerusalem, Jerusalem, Israel (Ringgold ID: RIN26742)
,
Zackaria Nairoukh 
1   Institute of Chemistry, Casali Center of Applied Chemistry, The Hebrew University of Jerusalem, Jerusalem, Israel (Ringgold ID: RIN26742)
› Author Affiliations
Supported by: Neubauer Foundation
Supported by: Casali Foundation Israel
Supported by: Israel Science Foundation 436/24
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We report a site- and regioselective Heck-type arylation reaction for the synthesis of highly substituted 1,2-dihydropyridines from simple pyridine precursors. This transformation serves as a key step in our previously developed stepwise dearomative multi-functionalization platform, enabling the syn-addition of aryl halides to dihydropyridine intermediates under mild conditions. Comprehensive scope studies demonstrate broad functional group tolerance, accommodating both electron-rich and electron-deficient aryl iodides, a variety of N-protecting groups, and diverse C2 substituents



Publication History

Received: 24 April 2025

Accepted after revision: 30 May 2025

Accepted Manuscript online:
30 May 2025

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