349407-14-3Relevant articles and documents
KMnO4-mediated oxidative C[sbnd]N bond cleavage of tertiary amines: Synthesis of amides and sulfonamides
Zhang, Zhang,Liu, Yong-Hong,Zhang, Xi,Wang, Xi-Cun
, p. 2763 - 2770 (2019/04/10)
KMnO4-mediated oxidative C[sbnd]N bond cleavage of tertiary amines producing secondary amine was introduced, which was trapped by electrophiles (acyl chloride and sulfonyl chloride) to form amides and sulfonamides. The reaction could take place at mild condition, tolerating a wide range of function groups and affording products in moderate to excellent yields.
The nBu4NI catalysed oxidative benzoic acid amide formation from aryl acetaldehydes and amines in aqueous solution
Song, Ge,Sun, Gangchun,Tang, Yamin,Mai, Wenpeng
, p. 630 - 632 (2013/11/06)
A metal-free amide synthesis from aryl acetaldehydes and secondary aromatic amines via a carbon degradation process using nBu4NI/TBHP system in aqueous solution is described. This protocol has not been reported previously. Both substrates are cheap and readily available.
NBu4NI-catalyzed unexpected amide bond formation between aldehydes and aromatic tertiary amines
Mai, Wen-Peng,Song, Ge,Yuan, Jin-Wei,Yang, Liang-Ru,Sun, Gang-Chun,Xiao, Yong-Mei,Mao, Pu,Qu, Ling-Bo
, p. 3869 - 3872 (2013/04/24)
A novel and practical amide bond formation method has been developed without the need for any metals. This method provides a novel route for amide bond formation, in the presence of an nBu4NI/TBHP catalyst system, from readily available aldehydes and aromatic tertiary amines.
DIRECT CONVERSION OF PHENOLS INTO AMIDES AND ESTERS OF BENZOIC ACID
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Page/Page column 15-16; 22, (2011/10/12)
A method is provided for the preparation of an aromatic carboxylic acid aryl ester or an N-aryl aromatic carboxamide. The method comprises contacting an O,O-diaryl thiocarbonate or an O-aryl-N-aryl thiocarbamate with a reactant that regioselectively reacts with sulfur, which contact causes an O-neophyl rearrangement, thereby forming either the aromatic carboxylic acid aryl ester or the N-aryl aromatic carboxamide, respectively.
Trimethylaluminium-facilitated direct amidation of carboxylic acids
Chung, Seungwon,Uccello, Daniel P.,Choi, Huiwon,Montgomery, Justin I.,Chen, Jinshan
scheme or table, p. 2072 - 2074 (2011/10/08)
Free carboxylic acids are converted into amides in moderate to high yields in the presence of a stoichiometric amount of trimethylaluminium and amines at 90°C after 1 hour. Georg Thieme Verlag Stuttgart - New York.
Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides
Baroudi, Abdulkader,Alicea, Jeremiah,Flack, Phillip,Kirincich, Jason,Alabugin, Igor V.
scheme or table, p. 1521 - 1537 (2011/06/11)
We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.
Metal-free transformation of phenols into substituted benzamides: A highly selective radical 1,2-O→C transposition in O-aryl-N-phenylthiocarbamates
Baroudi, Abdulkader,Flack, Phillip,Alabugin, Igor V.
experimental part, p. 12316 - 12320 (2010/12/29)
Radical merry-go-round: A highly efficient metal-free transformation of phenols into benzamides is designed through one-step conversion of phenols to aryl thiocarbamates and a subsequent radical addition/rearrangement/ fragmentation cascade. Computational analysis fully rationalizes the experimentally observed selectivity. Despite the possible competition from N-C fragmentation and N-neophyl rearrangement, the transformation exclusively follows the most kinetically and thermodynamically favored O-neophyl rearrangement path.
