Literature DB >> 26880039

Copper-Catalyzed Insertion into Heteroatom-Hydrogen Bonds with Trifluorodiazoalkanes.

Stephen Hyde1, Janis Veliks1, Benoît Liégault1,2, David Grassi1, Marc Taillefer2, Véronique Gouverneur3.   

Abstract

Copper-catalyzed Si-H, B-H, P-H, S-H, and N-H insertion reactions of 2,2,2-trifluoro-1-diazoethane and 1-aryl 2,2,2-trifluorodiazoethanes generated a large number of new fluorine-containing chemical entities for medicinal chemists. With selected Si-H and B-H insertion reactions, we demonstrate successful extension to asymmetric catalysis.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; carbenes; copper catalysis; diazo compounds; heteroatom-hydrogen insertion

Year:  2016        PMID： 26880039     DOI： 10.1002/anie.201511954

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  16 in total

1.  Mechanistic Investigation of Biocatalytic Heme Carbenoid Si-H Insertions.

Authors:  Rahul L Khade; Ajay L Chandgude; Rudi Fasan; Yong Zhang
Journal:  ChemCatChem       Date:  2019-05-08       Impact factor: 5.686

2.  Genetically programmed chiral organoborane synthesis.

Authors:  S B Jennifer Kan; Xiongyi Huang; Yosephine Gumulya; Kai Chen; Frances H Arnold
Journal:  Nature       Date:  2017-11-29       Impact factor: 49.962

3.  Enantiodivergent α-Amino C-H Fluoroalkylation Catalyzed by Engineered Cytochrome P450s.

Authors:  Juner Zhang; Xiongyi Huang; Ruijie K Zhang; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2019-06-12       Impact factor: 15.419

4.  Directed evolution of cytochrome c for carbon-silicon bond formation: Bringing silicon to life.

Authors:  S B Jennifer Kan; Russell D Lewis; Kai Chen; Frances H Arnold
Journal:  Science       Date:  2016-11-25       Impact factor: 47.728

5.  Highly Diastereo- and Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes via Myoglobin-Catalyzed Transfer of Trifluoromethylcarbene.

Authors:  Antonio Tinoco; Viktoria Steck; Vikas Tyagi; Rudi Fasan
Journal:  J Am Chem Soc       Date:  2017-04-10       Impact factor: 15.419

6.  "Sandwich" Diimine-Copper Catalysts for C-H Functionalization by Carbene Insertion.

Authors:  Kristine Klimovica; Julius X Heidlas; Irvin Romero; Thanh V Le; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-10       Impact factor: 16.823

7.  Enantioselective Diarylcarbene Insertion into Si-H Bonds Induced by Electronic Properties of the Carbenes.

Authors:  Liang-Liang Yang; Declan Evans; Bin Xu; Wen-Tao Li; Mao-Lin Li; Shou-Fei Zhu; K N Houk; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2020-07-01       Impact factor: 15.419

8.  Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B-H bond insertion reaction.

Authors:  Guan Zhang; Zhihan Zhang; Mengyuan Hou; Xinping Cai; Kai Yang; Peiyuan Yu; Qiuling Song
Journal:  Nat Commun       Date:  2022-05-12       Impact factor: 17.694

Review 9.  Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

Authors:  Weichao Xue; Martin Oestreich
Journal:  ACS Cent Sci       Date:  2020-07-09       Impact factor: 14.553

10.  Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.

Authors:  Xinyu Zhang; Zhaohong Liu; Xiangyu Yang; Yuanqing Dong; Matteo Virelli; Giuseppe Zanoni; Edward A Anderson; Xihe Bi
Journal:  Nat Commun       Date:  2019-01-17       Impact factor: 14.919
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