用于硫醇1,1-二氢氟烷基化反应的新型磺酰氟衍生的烷基化试剂。
New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols.
作者信息
Foth Paul J, Gu Frances, Bolduc Trevor G, Kanani Sahil S, Sammis Glenn M
机构信息
Department of Chemistry , University of British Columbia , 2036 Main Mall , Vancouver , British Columbia V6T 1Z1 , Canada . Email:
出版信息
Chem Sci. 2019 Sep 20;10(44):10331-10335. doi: 10.1039/c9sc03570b. eCollection 2019 Nov 28.
Herein, we report a new method for the one-pot synthesis of 1,1-dihydrofluoroalkyl sulfides by bubbling sulfuryl fluoride (SOF) through a solution of the corresponding alcohol and thiol. The reaction proceeds through a new class of bis(1,1-dihydrofluoroalkyl) sulfate reagents, to afford the desired 1,1-dihydrofluoroalkyl sulfides in 55-90% isolated yields. The bis(1,1-dihydrofluoroalkyl) sulfates are highly chemoselective for thiol alkylation, and are unreactive with competing, unprotected nucleophiles, including amines, alcohols, and carboxylic acids.
在此，我们报道了一种通过将硫酰氟（SOF）鼓泡通过相应醇和硫醇的溶液来一锅法合成1,1-二氢氟烷基硫醚的新方法。该反应通过一类新型的双（1,1-二氢氟烷基）硫酸盐试剂进行，以55-90%的分离产率得到所需的1,1-二氢氟烷基硫醚。双（1,1-二氢氟烷基）硫酸盐对硫醇烷基化具有高度的化学选择性，并且与包括胺、醇和羧酸在内的竞争性未保护亲核试剂不发生反应。
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