- One-step Conversion of Amides and Esters to Acid Chlorides with PCl3
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A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.
- Li, Fangshao,Wu, Xiaofang,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing
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supporting information
p. 4314 - 4317
(2021/07/16)
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- PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation
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A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.
- Wu, Xiaofang,Zhou, Lei,Li, Fangshao,Xiao, Jing
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p. 491 - 497
(2021/01/20)
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- A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides
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For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.
- Wu, Xiaofang,Zhou, Lei,Yang, Ruoqi,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing
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p. 301 - 304
(2020/01/29)
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- Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides
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A transition metal- and organophotocatalyst free synthesis of esters, carboxylic anhydrides and amides from aldehydes induced by visible-light has been reported. The proposed methodology can be carried out by the use of sunlight or artificial visible light as a blue LED source. The methodology has a very broad applicability and the desired products are obtained in very satisfactory yields.
- Gaspa, Silvia,Raposo, Inês,Pereira, Leonor,Mulas, Gabriele,Ricci, Pier Carlo,Porcheddu, Andrea,De Luca, Lidia
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supporting information
p. 10711 - 10715
(2019/07/15)
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- Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles
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A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.
- Shang, Ming,Sun, Shang-Zheng,Dai, Hui-Xiong,Yu, Jin-Quan
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supporting information
p. 3354 - 3357
(2014/03/21)
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- A palladium-catalyzed carbonylation approach to acid chloride synthesis
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We describe a new approach to acid chloride synthesis via the palladium-catalyzed carbonylation of aryl iodides. The combination of sterically encumbered phosphines (PtBu3) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from (tBu3P)(CO) Pd(COAr)Cl. The formation of acid chlorides can also be exploited to perform traditional aminocarbonylation reactions under exceptionally mild conditions (ambient temperature and pressure), and with a range of weakly nucleophilic substrates.
- Quesnel, Jeffrey S.,Arndtsen, Bruce A.
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supporting information
p. 16841 - 16844
(2013/12/04)
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- Process for preparing fluorine-containing benzaldehydes
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The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.
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- 1-amidooctahydropyrido[2,1-c][1,4]oxazine compounds
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The invention relates to the compounds of general formula STR1 in which R1, R2, R4, R5 and A are as defined in the description. their isomers, diastereoisomers, and enantiomers as well as their addition salts with a pharmaceutically acceptable inorganic or organic acid, and medicinal products containing the same which are usable for the treatment of psycho-behavioral disorders.
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- Pesticidal cyclic malonylphosphonic diamides
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Novel pesticidally active cyclic malonylphosphonic diamides of the formula STR1 in which X represents O or S, R1 represents alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heteroaryl, each of which can be optionally substituted, R2 represents hydrogen, alkyl, aryl or aralkyl, R3 represents hydrogen, alkyl, aryl or aralkyl, and R4 represents an acyl radical, or salts thereof, Many intermediates are new,
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- Insecticidal cyclopropyl-substituted di(aryl) compounds
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Compounds of the formula STR1 in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
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- The Synthesis of Fluorine Containing Phenyl Benzoates and Their Properties as Liquid Crystals
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A new series of fluorine containing phenyl benzoates has been synthesized and the transition temperatures of these compounds have been determined.A series of 4-trifluoromethylphenyl 4-n-alkylbenzoates showed no liquid crystalline behaviour, but the 4-trifluoromethylphenyl 4-n-alkoxybenzoates series, with six carbons or more in alkoxy chain, was mesomorphic.The 4-cyanophenyl 4-perfluoroalkylbenzoates showed smectic liquid crystalline properties.
- Misaki, S.,Takamatsu, S.,Suefuji, M.,Mitote, T.,Matsumura, M.
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p. 123 - 132
(2007/10/02)
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