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A one-pot synthesis of thioesters directly from carboxylic acids, N,N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4- (dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the quaternary ammonium salts, derived from alkyl halides and tertiary amines, were the intermediates to yield thioesters. A new reaction mechanism for this thioesterification is proposed.
|Number of pages||8|
|Journal||Journal of Organic Chemistry|
|State||Published - 6 Oct 2017|
FingerprintDive into the research topics of 'Microwave-assisted direct thioesterification of carboxylic acids'. Together they form a unique fingerprint.
- 2 Finished
Further Synthesis of Brevipolides and Preparation of New Natural Products with Biological Activities.( II )
1/08/16 → 31/07/17
1/08/15 → 31/07/16