化学
脱质子化
碳负离子
酮
试剂
亲核细胞
猝灭(荧光)
碎片(计算)
群(周期表)
功能群
药物化学
有机化学
组合化学
催化作用
离子
物理
聚合物
量子力学
计算机科学
荧光
操作系统
作者
Patrick S. Fier,Riley Roberts,Reed T. Larson
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-04-26
卷期号:25 (17): 3131-3135
被引量:2
标识
DOI:10.1021/acs.orglett.3c00992
摘要
We report here the design and development of a method for the single-step conversion of esters to ketones with simple reagents. The selective transformation of esters to ketones, rather than tertiary alcohols, is made possible by the use of a transient sulfinate group on the nucleophile that activates the adjacent carbon toward deprotonation to form a carbanion that adds to the ester, followed by a second deprotonation to prevent further addition. The resulting dianion undergoes spontaneous fragmentation of the SO2 group upon quenching with water to reveal the ketone product.
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