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DOI: 10.1055/s-0040-1720148
Palladium-Catalyzed α-Arylation of Cycloalkanones with Sterically Hindered Bromoazines under Neat Conditions
Abstract
The palladium-catalyzed cross-coupling of cycloalkanones with a range of heteroaryl bromides is described herein. The transformation proceeds best with third-generation tris-tBu-phosphine Pd pre-catalyst in neat cycloalkanones. Careful screening of the reaction conditions revealed K3PO4 as an effective weak and mild base thereby tolerating base-sensitive functional groups such as acetals or nitrogen protecting groups. Moderate to good yields were achieved for a series of 29 examples with various degrees of structural complexity. Importantly, these optimized conditions allow the α-(hetero)aryl cross-coupling of ortho-substituted (hetero)aryl bromide substrates with different cycloalkanones that typically failed to react efficiently under previously reported conditions.
Key words
palladium catalysis - α-arylation - cycloalkanones - bromoazines - third-generation tris-tBu-phosphine Pd pre-catalyst - neat conditionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720148.
- Supporting Information
Publication History
Received: 03 September 2024
Accepted: 19 September 2024
Article published online:
22 October 2024
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