Literature DB >> 35594167

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

Kristine Klimovica1, Julius X Heidlas1, Irvin Romero1, Thanh V Le1, Olafs Daugulis1.   

Abstract

We report here "sandwich" diimine-copper(I) catalysts for C(sp3 )-H bond functionalization. Reactions of alkanes and ethers with trimethylsilyldiazomethane, ethyl diazoacetate, and trifluoromethyl-diazomethane have been demonstrated. We also report C(sp3 )-H bond methylation, benzylation, and diphenylmethylation by diazomethane, aryldiazomethanes, and diphenyldiazomethane. These reactions are rare examples of base-metal catalyzed, intermolecular C(sp3 )-H functionalizations by employing unactivated diazo compounds. Electrophilicity and unique steric environment of "sandwich"-copper catalysts are likely reasons for their catalytic efficiency.
© 2022 Wiley-VCH GmbH.

Entities:  

Keywords:  Carbenes; Copper; C−H Activation; Diazo Compounds; Diimines

Year:  2022        PMID： 35594167      PMCID： PMC9329213          DOI： 10.1002/anie.202200334

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   16.823


  46 in total

1.  Copper(I) Carbenes: The Synthesis of Active Intermediates in Copper-Catalyzed Cyclopropanation B.F.S. thanks the Fonds der Chemischen Industrie for a doctoral fellowship.

Authors:  Bernd F. Straub; Peter Hofmann
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-01       Impact factor: 15.336

2.  Intermolecular copper-catalyzed carbon [bond] hydrogen bond activation via carbene insertion.

Authors:  M Mar Díaz-Requejo; Tomás R Belderraín; M Carmen Nicasio; Swiatoslaw Trofimenko; Pedro J Pérez
Journal:  J Am Chem Soc       Date:  2002-02-13       Impact factor: 15.419

Review 3.  Catalytic carbene insertion into C-H bonds.

Authors:  Michael P Doyle; Richard Duffy; Maxim Ratnikov; Lei Zhou
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

4.  C-H functionalization logic in total synthesis.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  Chem Soc Rev       Date:  2011-02-07       Impact factor: 54.564

5.  3d Transition Metals for C-H Activation.

Authors:  Parthasarathy Gandeepan; Thomas Müller; Daniel Zell; Gianpiero Cera; Svenja Warratz; Lutz Ackermann
Journal:  Chem Rev       Date:  2018-11-27       Impact factor: 60.622

6.  Ruthenium-porphyrin-catalyzed diastereoselective intramolecular alkyl carbene insertion into C-H bonds of alkyl diazomethanes generated in situ from N-tosylhydrazones.

Authors:  Annapureddy Rajasekar Reddy; Cong-Ying Zhou; Zhen Guo; Jinhu Wei; Chi-Ming Che
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-15       Impact factor: 15.336

Review 7.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

Review 8.  Enantioselective C(sp3)‒H bond activation by chiral transition metal catalysts.

Authors:  Tyler G Saint-Denis; Ru-Yi Zhu; Gang Chen; Qing-Feng Wu; Jin-Quan Yu
Journal:  Science       Date:  2018-02-16       Impact factor: 47.728

9.  Catalytic functionalization of low reactive C(sp(3))-H and C(sp(2))-H bonds of alkanes and arenes by carbene transfer from diazo compounds.

Authors:  Ana Caballero; M Mar Díaz-Requejo; Manuel R Fructos; Andrea Olmos; Juan Urbano; Pedro J Pérez
Journal:  Dalton Trans       Date:  2015-11-16       Impact factor: 4.390

10.  Enantioselective Si-H Insertion Reactions of Diarylcarbenes for the Synthesis of Silicon-Stereogenic Silanes.

Authors:  Jake R Jagannathan; James C Fettinger; Jared T Shaw; Annaliese K Franz
Journal:  J Am Chem Soc       Date:  2020-06-24       Impact factor: 15.419
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