Use of dipyridyldithiocarbonate (DPDTC) as an environmentally responsible reagent leading to esters and thioesters under green chemistry conditions
Use of dipyridyldithiocarbonate (DPDTC) as an environmentally responsible reagent leading to esters and thioesters under green chemistry conditions
复制标题
DOI：
10.1039/d3gc03093h
复制
发表时间：
2023-11-09
期刊：
影响因子：
9.8
通讯作者：
Lipshutz，Bruce H.
中科院分区：
文献类型：
--
作者：
Freiberg，Kaitlyn M.;Ghiglietti，Erika;Lipshutz，Bruce H.
基于二吡啶二硫代氨基甲酸酯（DPDTC）原位生成2-硫代吡啶酯的中间体，发展了一种新的绿色酯化和硫代酯化方法。两者都是通过在纯条件下用DPDTC初始处理相应的羧酸，然后在浓EtOAc中或在水性胶束条件下引入醇或硫醇以及催化量的活化基团而形成的。这些一锅法产生高产率的酯和硫酯，避免使用传统的偶联剂，并导致最小的废物产生，因为EtOAc和硫醇副产物都很容易再循环。
A new, green esterification and thioesterification method has been developed based on the intermediacy of in situ-generated 2-thiopyridine esters derived from dipyridyldithiocarbamate (DPDTC). Both are formed from initial treatment of the corresponding carboxylic acid with DPDTC under neat conditions, followed by introduction of the alcohol or thiol, together with catalytic amounts of an activating group, in concentrated EtOAc or under aqueous micellar conditions. These 1-pot processes generate high yields of esters and thioesters, avoid use of traditional coupling agents, and lead to minimal waste creation as both the EtOAc and the thiol by-product are easily recycled.