86561-27-5Relevant articles and documents
Study of the Rh2(OAc)4- or BF3·OEt2-mediated reaction of thioacetic S-acid with α-diazocarbonyl compounds
Yao, Wengang,Liao, Mingyi,Zhang, Xiaomei,Xu, Hao,Wang, Jianbo
, p. 1784 - 1788 (2003)
The Rh2(OAc)4-catalyzed reaction of methyl aryldiazo-acetates with thioacetic S-acid gives exclusively the S-H insertion products in high yields, while the corresponding reaction mediated by BF3·OEt2 gives O-est
Tropylium-Catalyzed O-H Insertion Reactions of Diazoalkanes with Carboxylic Acids
Empel, Claire,Nguyen, Thanh Vinh,Koenigs, Rene M.
supporting information, p. 548 - 553 (2021/01/26)
Herein, we describe the application of a nonbenzenoid aromatic carbocation, namely tropylium, as an organic Lewis acid catalyst in O-H functionalization reactions of diazoalkanes with benzoic acids. The newly developed protocol is applicable to a wide range of diazoalkane and carboxylic acid substrates with excellent efficiency (43 examples, up to 99% yield).
Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated by SO2F2 for Synthesis of Esters from Amides
Fang, Wan-Yin,Zha, Gao-Feng,Qin, Hua-Li
supporting information, p. 8657 - 8661 (2019/10/17)
We discovered that with the promotion of sulfuryl fluoride, the carbonyl groups of amides performed as nucleophiles while the hydroxyl groups of alcohols were activated to functionalize as electrophiles. This study displayed that the amide C-N bonds could be easily cleaved with delicate nucleophiles to form the ester C-O bonds at room temperature without using transition metals. The broad substrate scope and excellent functional group compatibility were proved with 44 examples in up to 99% yields.