Literature DB >> 30868885

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO.

Wan-Yin Fang1, Hua-Li Qin1.   

Abstract

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

Entities:  

Year:  2019        PMID: 30868885     DOI: 10.1021/acs.joc.8b03164

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  HCl•DMPU-Assisted One-pot and Metal-free Conversion of Aldehydes to Nitriles.

Authors:  Sagar R Mudshinge; Chinmay S Potnis; Bo Xu; Gerald B Hammond
Journal:  Green Chem       Date:  2020-05-14       Impact factor: 10.182

2.  Process Development of the Copper(II)-Catalyzed Dehydration of a Chiral Aldoxime and Rational Selection of the Co-Substrate.

Authors:  Jannis Nonnhoff; Harald Gröger
Journal:  ChemistryOpen       Date:  2021-12-10       Impact factor: 2.630

3.  SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN).

Authors:  Yiyong Zhao; Junjie Wei; Shuting Ge; Guofu Zhang; Chengrong Ding
Journal:  RSC Adv       Date:  2020-05-04       Impact factor: 4.036

4.  SO2F2 mediated cascade dehydrogenative Morita-Baylis-Hillman reaction of the C(sp3)-H of primary alcohols with the C(sp2)-H of electron-deficient olefins for the assembly of allylic alcohols.

Authors:  Ying Jiang; Njud S Alharbi; Bing Sun; Hua-Li Qin
Journal:  RSC Adv       Date:  2019-09-20       Impact factor: 3.361

5.  New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols.

Authors:  Paul J Foth; Frances Gu; Trevor G Bolduc; Sahil S Kanani; Glenn M Sammis
Journal:  Chem Sci       Date:  2019-09-20       Impact factor: 9.825

6.  Rapid and column-free syntheses of acyl fluorides and peptides using ex situ generated thionyl fluoride.

Authors:  Cayo Lee; Brodie J Thomson; Glenn M Sammis
Journal:  Chem Sci       Date:  2021-11-29       Impact factor: 9.825

  6 in total

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