Continuous Flow Synthesis of α-Trifluoromethylthiolated Esters and Amides from Carboxylic Acids: a Telescoped Approach

被引：5

作者：

Franco, Francesca ^{[1
]}

Meninno, Sara ^{[1
]}

Lattanzi, Alessandra ^{[1
]}

Puglisi, Alessandra ^{[2
]}

Benaglia, Maurizio ^{[2
]}

机构：

[1] Univ Salerno, Dipartimento Chim & Biol A Zambelli, I-84084 Fisciano, Italy

[2] Univ Milan, Dipartimento Chim, I-20133 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 20期

基金：

欧盟地平线“2020”;

关键词：

CHEMISTRY; FLUORINE;

D O I：

10.1021/acs.joc.1c01270

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A continuous flow approach to access alpha-trifluoromethylthiolated esters and amides using commercially available arylacetic acids and N-(trifluoromethylthio)phthalimide as the electrophilic reagent is described. The experimental protocol involves the in-flow conversion of the carboxylic acid into N-acylpyrazole followed by the alpha-trifluoromethylthiolation in a PTFE coil reactor and final reaction with primary or secondary amines, or alcohols, to afford in a telescoped process alpha-substituted SCF3 amides and esters, respectively, in good overall yield and short reaction times.

引用

页码：14207 / 14212

页数：6

共 50 条

[21] A Photochemical Protocol for the Synthesis of Weinreb and Morpholine Amides from Carboxylic Acids
Bourboula, Asimina
Mountanea, Olga G.
Krasakis, George
Mantzourani, Christiana
Kokotou, Maroula G.
Kokotos, Christoforos G.
Kokotos, George
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (24)
[22] Triphenyl borate catalyzed synthesis of amides from carboxylic acids and amines
Ghorpade, Seema A.
Sawant, Dinesh N.
Sekar, Nagaiyan
TETRAHEDRON, 2018, 74 (48) : 6954 - 6958
[23] SYNTHESIS OF AMIDES FROM CARBOXYLIC-ACIDS AND AMINES IN PRESENCE OF ISOCYANIDES
AIGNER, H
MARQUARDING, D
TETRAHEDRON LETTERS, 1978, (36) : 3325 - 3326
[24] Ce(III)/Photoassisted Synthesis of Amides from Carboxylic Acids and Isocyanates
Li, Hao-Cong
Li, Guan-Nan
Sun, Kai
Chen, Xiao-Lan
Jiang, Ming-Xuan
Qu, Ling-Bo
Yu, Bing
ORGANIC LETTERS, 2022, 24 (12) : 3431 - 3435
[25] Synthesis of Carboxylic Acids and Esters from CO2
Wu, Xiao-Feng
Zheng, Feng
TOPICS IN CURRENT CHEMISTRY, 2017, 375 (01)
[26] Synthesis of Carboxylic Acids and Esters from CO2
Xiao-Feng Wu
Feng Zheng
Topics in Current Chemistry, 2017, 375
[27] Direct amidation of acids in a screw reactor for the continuous flow synthesis of amides
Atapalkar, Ranjit S.
Kulkarni, Amol A.
CHEMICAL COMMUNICATIONS, 2023, 59 (60) : 9231 - 9234
[28] Difluoromethylene compounds as precursors to ketones, carboxylic acids, esters, amides and carbonates
Guo, Yong
Shreeve, Jean'ne M.
JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (10) : 1280 - 1285
[29] INTERACTION OF AMIDES OF PYROCATECHOLPHOSPHORIC ACID WITH SILYLATED ESTERS OF CARBOXYLIC-ACIDS
PUDOVIK, MA
KIBARDINA, LK
PUDOVIK, AN
ZHURNAL OBSHCHEI KHIMII, 1991, 61 (06): : 1473 - 1474
[30] A new enzymatic one-pot procedure for the synthesis of carboxylic amides from carboxylic acids
deZoete, MC
KockvanDalen, AC
vanRantwijk, F
Sheldon, RA
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1996, 2 (01) : 19 - 25

← 1 2 3 4 5 →