AI Article Synopsis
- Fluorinated compounds are important in pharmaceuticals and agrochemicals, and this study focuses on synthesizing a specific type of benzamide using a rhodium(III) catalyst.
- The new method shows versatility as it works well with a variety of substrates, tolerates different functional groups, is easily scalable, and has high selectivity in the synthesis process.
- Notably, the reaction is efficient without the need for external oxidants, allowing for innovative synthesis of complex difluorinated molecules from commonly available starting materials.
Article Abstract
Fluorinated molecules are widely used in pharmaceutical and agrochemical industries. Herein we report the synthesis of 2-(3,3-difluoro-4-(silyloxy)but-1-en-1-yl)benzamides from the unprecedented rhodium(III)-catalyzed alkenylation of various benzamides with difluorohomoallylic silyl ethers. The practicability of this protocol is demonstrated by its broad substrate compatibility, good functional group tolerance, ready scalability and high regioselectivity. The oxygen in difluorohomoallylic silyl ethers makes β-H elimination feasible, which suppresses both the β-F elimination and dialkenylation of benzamides. This redox-neutral reaction proceeds efficiently N-O bond cleavage without external oxidants and thus provides new opportunities for the synthesis of elaborate difluorinated compounds from readily available fluorinated synthons.
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