Ho Johnson H, Miller Grant H, Chung Kasey K, Neibert Sydney D, Beutner Gregory L, Vosburg David A
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, California 91711, United States.
Chemical Process Development, Bristol Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Org Lett. 2024 Oct 18;26(41):8904-8909. doi: 10.1021/acs.orglett.4c03363. Epub 2024 Oct 7.
,,','-Tetramethylchloroformamidinium hexafluorophosphate (TCFH) and -methylimidazole (NMI) enable the facile and practical reaction of carboxylic acids with amines, alcohols, and thiols to form amides, esters, and thioesters. To develop a mild synthesis of ketones with TCFH-NMI directly from carboxylic acids at room temperature, the Mayr nucleophilicity scale was used to compare the values of competent nucleophiles to potential carbon-centered nucleophiles, identifying pyrroles and indoles as successful substrates when ≥ 10.
四甲基氯甲脒六氟磷酸盐（TCFH）和N - 甲基咪唑（NMI）可使羧酸与胺、醇和硫醇轻松且实际地反应形成酰胺、酯和硫酯。为了在室温下用TCFH - NMI直接从羧酸开发一种温和的酮合成方法，使用迈尔亲核性标度来比较活性亲核试剂与潜在碳中心亲核试剂的N值，当N≥10时，确定吡咯和吲哚为成功的底物。
