Literature DB >> 22920795

Metal-free N-H insertions of donor/acceptor carbenes.

Stephanie R Hansen1, Jillian E Spangler, Jørn H Hansen, Huw M L Davies.   

Abstract

Synthetically useful transformations arise from the thermal decomposition of aryldiazoacetates in the presence of primary and secondary amines without the use of a metal catalyst. Thermally generated, free donor/acceptor carbenes directly undergo N-H insertion with amines through selective aza-ylide formation to afford a variety of α-amino esters in 53-96% yields.

Entities:  

Year:  2012        PMID: 22920795     DOI: 10.1021/ol3020754

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Aminofluorination: transition-metal-free N-F bond insertion into diazocarbonyl compounds.

Authors:  Gui Chen; Jinshuai Song; Yinghua Yu; Xuesong Luo; Chunsen Li; Xueliang Huang
Journal:  Chem Sci       Date:  2015-12-14       Impact factor: 9.825

2.  Cyclopropanations via Heme Carbenes: Basic Mechanism and Effects of Carbene Substituent, Protein Axial Ligand, and Porphyrin Substitution.

Authors:  Yang Wei; Antonio Tinoco; Viktoria Steck; Rudi Fasan; Yong Zhang
Journal:  J Am Chem Soc       Date:  2018-01-24       Impact factor: 15.419

3.  α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions.

Authors:  Asmund Kaupang; Tore Bonge-Hansen
Journal:  Beilstein J Org Chem       Date:  2013-07-11       Impact factor: 2.883

4.  Blue light-promoted photolysis of aryldiazoacetates.

Authors:  Igor D Jurberg; Huw M L Davies
Journal:  Chem Sci       Date:  2018-05-22       Impact factor: 9.825

5.  Visible Light Induced Metal-Free Carbene N-Carbazolation.

Authors:  Claire Empel; Frederic W Patureau; Rene M Koenigs
Journal:  J Org Chem       Date:  2019-08-15       Impact factor: 4.354

6.  Metal-free tandem carbene N-H insertions and C-C bond cleavages.

Authors:  Pu Chen; Jiang Nan; Yan Hu; Yifan Kang; Bo Wang; Yangmin Ma; Michal Szostak
Journal:  Chem Sci       Date:  2020-11-10       Impact factor: 9.825

  6 in total

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