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Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated by SO2F2 for Synthesis of Esters from Amides.
Org Lett 2019; 21(21):8657-8661OL

Abstract

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.

Authors+Show Affiliations

State Key Laboratory of Silicate Materials for Architectures and School of Chemistry, Chemical Engineering and Life Sciences , Wuhan University of Technology , 205 Luoshi Road , Wuhan 430070 , P. R. China.State Key Laboratory of Silicate Materials for Architectures and School of Chemistry, Chemical Engineering and Life Sciences , Wuhan University of Technology , 205 Luoshi Road , Wuhan 430070 , P. R. China.State Key Laboratory of Silicate Materials for Architectures and School of Chemistry, Chemical Engineering and Life Sciences , Wuhan University of Technology , 205 Luoshi Road , Wuhan 430070 , P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31603334

Citation

Fang, Wan-Yin, et al. "Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated By SO2F2 for Synthesis of Esters From Amides." Organic Letters, vol. 21, no. 21, 2019, pp. 8657-8661.
Fang WY, Zha GF, Qin HL. Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated by SO2F2 for Synthesis of Esters from Amides. Org Lett. 2019;21(21):8657-8661.
Fang, W. Y., Zha, G. F., & Qin, H. L. (2019). Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated by SO2F2 for Synthesis of Esters from Amides. Organic Letters, 21(21), pp. 8657-8661. doi:10.1021/acs.orglett.9b03274.
Fang WY, Zha GF, Qin HL. Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated By SO2F2 for Synthesis of Esters From Amides. Org Lett. 2019 Nov 1;21(21):8657-8661. PubMed PMID: 31603334.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated by SO2F2 for Synthesis of Esters from Amides. AU - Fang,Wan-Yin, AU - Zha,Gao-Feng, AU - Qin,Hua-Li, Y1 - 2019/10/11/ PY - 2019/10/12/pubmed PY - 2019/10/12/medline PY - 2019/10/12/entrez SP - 8657 EP - 8661 JF - Organic letters JO - Org. Lett. VL - 21 IS - 21 N2 - 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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/31603334/Making_Carbonyls_of_Amides_Nucleophilic_and_Hydroxyls_of_Alcohols_Electrophilic_Mediated_by_SO2F2_for_Synthesis_of_Esters_from_Amides L2 - https://dx.doi.org/10.1021/acs.orglett.9b03274 DB - PRIME DP - Unbound Medicine ER -