Amide Formation Using In Situ Activation of Carboxylic Acids with [Et₂NSF₂]BF₄

Abstract

The formation of amides through the in situ activation of carboxylic acids with [Et2NSF2]BF4 is presented. A wide range of carboxylic acids and amines were used to produce the corresponding amides in up to 99 % yield. The reaction of hindered amines was also possible in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) under slightly modified conditions. An enantiopure carboxylic acid and amine were both shown to react without racemization.

Synthesis and Antibacterial Activity of Difluoromethyl Cinnamoyl Amides

“…The key step in this synthetic approach was the double deoxofluorination of the cinnamic acid derivative 9 to give 3 -difluoromethyl-4 -methoxycinnamoyl fluoride (10) and its subsequent conversion to amides 11a-11m in a one pot procedure (Table 1). At this stage, Deoxofluor ® was chosen as the fluorinating reagent, as initial attempts to use XtalFluor-E ® were unsuccessful due to long reaction times and undesired byproducts [30]. However, one drawback of using Deoxofluor ® is the formation of N,N-bis(2-methoxyethyl)amine as a byproduct that can react with the acyl fluoride (Table 1, Method B), thus limiting the scope of the method to amines that are more nucleophilic than N,N-bis(2-methoxyethyl)amine [31][32][33][34].…”

Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

“…Although sluggish via this method, the carbonylation of aryl chlorides at ambient temperature via conventional transition metal catalysis has not been realized due to the high energy barrier for oxidative addition of the transition metal catalyst to aryl chloride. 21 We are currently investigation conditions to accelerate the reduction of aryl chlorides using tandem photoredox catalysis. Notably, the method was compatible with electron-rich and deficient heteroaryl halides (21a-22).…”

Reduction of N-Allylamides by LiAlH4: Unexpected Attack of the Double Bond with Mechanistic Studies of Product and Byproduct Formation

“…This compound has also been synthesized by Mahé et al using a different method . In a dried flask under an atmosphere of nitrogen was prepared a solution of allylamine ( 3 ) (8.98 mL, 120 mmol) in CH 2 Cl 2 (120 mL).…”

“…IR (ATR): 3287 (br s), 3077 (w), 2963 (s), 2928 (s), 2876 (m), 2862 (m), 1637 (s), 1538 (s), 1238 (m), 925 (s), 709 (s) cm −1 . HRMS (EI-TOF) m/z: [M] + calcd for C 9 H 17 N 1 O 1 155.1310; found 155.1306.N-Allyl-2-phenylacetamide (19) 58. This compound has also been synthesized by Mahéet al using a different method 58.…”

“…HRMS (EI-TOF) m/z: [M] + calcd for C 9 H 17 N 1 O 1 155.1310; found 155.1306.N-Allyl-2-phenylacetamide (19) 58. This compound has also been synthesized by Mahéet al using a different method 58. In a dried flask under an atmosphere of nitrogen was prepared a solution of allylamine (3) (8.98 mL, 120 mmol) in CH 2 Cl 2 (120 mL).…”