5H-3-oxa-Octafluoropentanesulfonyl fluoride: a novel and efficient condensing agent for esterification, amidation and anhydridization

Discovery of KOH/BrCH2SO2F as Water‐Removable System for Clean, Mild and Robust Synthesis of Amides and Peptides

“…Comparing with organic bases, the inorganic ones usually feather with easy separation and formation of relatively benign by‐products, which enable them to be more attractive and desirable for organic synthesis [14] . A perusal of the literature reveals that sulfonyl fluorides (R‐SO 2 F) and most of the classical coupling reagents were usually used in combination with large excess of organic bases for amide synthesis, such as the systems of PyBOP+DIPEA, [15] HBTU+DIPEA, [16] HATU+ DIPEA, [17] DEPBT+DIPEA, [18] SO 2 F 2 +DIPEA, [11e] HCF 2 CF 2 OCF 2 CF 2 SO 2 F+DBU, [11c] and benzene‐1,3‐disulfonyl fluoride+DIPEA+DBU, [11a] most of which produced large amounts of organic waste together with necessary tedious work‐up and purification (Scheme 1b). Herein, we discovered a novel coupling system of using the combination of bromomethanesulfonyl fluoride (BMSF) with inorganic base KOH as water‐removable system for mild, green and practical synthesis of amides and peptides (Scheme 1c).…”

One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride

“…在此基础上, 近年来, 我们课题组扩 展了它在有机合成化学中的使用范围, 并成功地将其应 用于 C-O [6] , C-N 和 C-S [7] 键的构建中. 我们的实验 结果发现 R f SO 2 F 可以被扩展用于活化羧酸 [ 8 ] 、醛 肟 [9] 和酮肟 [10] 中的羟基而发生酯化、酰胺化和贝克曼重 排等反应. 最近我们还报道了全氟烷基磺酰氟应用于活 化二苯基膦氧和醇之间的 Arthen-Todd-like 反应生成了 相应的膦酸酯化合物 [11] .…”

One-Step C- or O-Benzylation of 1,3-Dicarbonyls with Benzyl Alcohols Promoted by Perfluoroalkanosulfonyl Fluoride

“…在此基础上, 我们近年来陆陆续续地 报道了一些 R f SO 2 F 应用于 C-O [11] , C-N 和 C-S [12] 键构建的研究结果. R f SO 2 F 除了可以活化醇羟基外, 还 可以用于活化羧酸 [13] 、 醛肟 [14] 和酮肟 [15] 中的羟基而发生 酯化、酰胺化和贝克曼重排等反应. 全氟烷基磺酰氟还 可作用于特殊刚性结构的羟基酮化合物而巧妙地应用 于分子内 C-C 键构建中 [16] 以及作为氧化体系的组成部 分应用于烯烃的环氧化 [17] 和苄醇的氧化反应 [18] 中.…”