- Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required
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A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.
- Kwon, Young-Do,La, Minh Thanh,Kim, Hee-Kwon
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p. 10833 - 10841
(2018/07/05)
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- Convenient metal-free direct oxidative amidation of aldehyde using dibromoisocyanuric acid under mild conditions
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A facile method for the direct synthesis of amides from aldehydes is described. Amide bonds were synthesized by an oxidative amidation in the presence of dibromoisocyanuric acid (DBI). Treatment of aromatic and aliphatic aldehydes with dibromoisocyanuric acid generated acyl bromide intermediates, which were employed to react with a variety of secondary and primary amines to give amides. Through this reaction method, various amides were synthesized directly from aldehydes under mild conditions in high yields and short times. This facile and efficient procedure provides potential strategy for the direct synthesis of amides from aldehydes.
- Kang, Soosung,La, Minh Thanh,Kim, Hee-Kwon
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supporting information
p. 3541 - 3546
(2018/08/29)
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- Appel reaction of carboxylic acids with tribromoisocyanuric acid/triphenylphosphine: A mild and acid-free preparation of esters and amides
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A facile and efficient method for esterification and amidation of carboxylic acids under neutral conditions has been developed. Esters and amides can be prepared by reacting a carboxylic acid (1 mmol) with tribromoisocyanuric acid (0.37 mmol) and triphenylphosphine (1 mmol) in dichloromethane at room temperature, followed by addition of an alcohol or an amine, respectively.
- Da Cunha Sindra, Haryadylla,De Mattos, Marcio C.S.
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p. 1129 - 1136
(2016/07/06)
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- FORMATION OF ACYL BROMIDES FROM CARBOXYLIC ACIDS AND N-BROMOSUCCINIMIDE; SOME REACTIONS OF BROMOCYANOTRIPHENYLPHOSPHORANE
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Acyl halides, i.e., acyl bromides and acyl chlorides can be generated in high yields under mild conditions from the corresponding carboxylic acid in the presence of equivalent amounts of NBS/NCS and triphenylphosphine.The reaction between carboxylic acids, bromocyane and triphenylphosphine (Ph3PBrCN), affords under similar conditions acyl bromides.Bromocyanotriphenylphosphorane reacts also smoothly with epoxides, e.g., phenyloxirane. it appears, however, that the expected bromocyanides are not obtainable by this reaction, vicinal dibromides being formed instead.Key words: Acyl bromides, synthesis of from carboxylic acids and NBS, bromocyanotriphenylphosphorane, synthesis of alkylhalides.
- Froeyen, Paul
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p. 253 - 260
(2007/10/02)
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