Literature DB >> 27936637

Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

Joshua R Hummel1, Jeffrey A Boerth1, Jonathan A Ellman1.   

Abstract

The transition-metal-catalyzed addition of C-H bonds to carbonyls, imines, and related polarized π bonds has emerged as a particularly efficient and powerful approach for the construction of an incredibly diverse array of heteroatom-substituted products. Readily available and stable inputs are typically employed, and reactions often proceed with very high functional group compatibility and without the production of waste byproducts. Additionally, many transition-metal-catalyzed C-H bond additions to polarized π bonds occur within cascade reaction sequences to provide rapid access to a diverse array of different heterocyclic as well as carbocyclic products. This review highlights the diversity of transformations that have been achieved, catalysts that have been used, and types of products that have been prepared through the transition-metal-catalyzed addition of C-H bonds to carbonyls, imines, and related polarized π bonds.

Entities:  

Year:  2016        PMID: 27936637      PMCID: PMC5468517          DOI: 10.1021/acs.chemrev.6b00661

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  127 in total

1.  Enantioselective rhodium(I)-catalyzed [3+2] annulations of aromatic ketimines induced by directed C-H activations.

Authors:  Duc N Tran; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-04       Impact factor: 15.336

2.  Rhodium-catalyzed direct addition of aryl C-H bonds to N-sulfonyl aldimines.

Authors:  Yang Li; Bi-Jie Li; Wen-Hua Wang; Wei-Ping Huang; Xi-Sha Zhang; Kang Chen; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-26       Impact factor: 15.336

3.  Expedient synthesis of N-acyl anthranilamides and β-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C-H bonds with isocyanates.

Authors:  Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2011-07-08       Impact factor: 15.419

4.  Rhodium-catalyzed oxidative ortho-acylation of benzamides with aldehydes: direct functionalization of the sp2 C-H bond.

Authors:  Jihye Park; Eonjeong Park; Aejin Kim; Youngil Lee; Ki-Whan Chi; Jong Hwan Kwak; Young Hoon Jung; In Su Kim
Journal:  Org Lett       Date:  2011-07-27       Impact factor: 6.005

5.  Rhenium-catalyzed diastereoselective synthesis of aminoindanes via the insertion of allenes into a C-H bond.

Authors:  Yoichiro Kuninobu; Peng Yu; Kazuhiko Takai
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

6.  Low-valent cobalt catalysis: new opportunities for C-H functionalization.

Authors:  Ke Gao; Naohiko Yoshikai
Journal:  Acc Chem Res       Date:  2014-02-27       Impact factor: 22.384

7.  Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes.

Authors:  Kevin G M Kou; Lauren E Longobardi; Vy M Dong
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

8.  Synthesis of indene frameworks via rhodium-catalyzed cascade cyclization of aromatic ketone and unsaturated carbonyl compounds.

Authors:  Xian-Ying Shi; Chao-Jun Li
Journal:  Org Lett       Date:  2013-03-07       Impact factor: 6.005

9.  Rh-catalyzed C-C cleavage of benzyl/allylic alcohols to produce benzyl/allylic amines or other alcohols by nucleophilic addition of intermediate rhodacycles to aldehydes and imines.

Authors:  Xi-Sha Zhang; Yang Li; Hu Li; Kang Chen; Zhi-Quan Lei; Zhang-Jie Shi
Journal:  Chemistry       Date:  2012-10-18       Impact factor: 5.236

10.  Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of α-Amino Acids.

Authors:  Apiwat Wangweerawong; Joshua R Hummel; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2016-02-04       Impact factor: 4.354

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  40 in total

1.  Three-Component Coupling of Aldehydes, 2-Aminopyridines, and Diazo Esters via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrido[1,2- a]pyrimidin-4-ones.

Authors:  Gia L Hoang; Adam J Zoll; Jonathan A Ellman
Journal:  Org Lett       Date:  2019-03-21       Impact factor: 6.005

2.  Cobalt(III)-Catalyzed Diastereoselective Three-Component C-H Bond Addition to Butadiene and Activated Ketones.

Authors:  Zican Shen; Chen Li; Brandon Q Mercado; Jonathan A Ellman
Journal:  Synthesis (Stuttg)       Date:  2019-11-07       Impact factor: 3.157

3.  Cobalt(III)-Catalyzed C-H Amidation of Dehydroalanine for the Site-Selective Structural Diversification of Thiostrepton.

Authors:  Ryan J Scamp; Edward deRamon; Eric K Paulson; Scott J Miller; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-27       Impact factor: 15.336

4.  A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)-Catalyzed Three-Component C-H Bond Addition.

Authors:  Jeffrey A Boerth; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-17       Impact factor: 15.336

5.  Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrazolo[1,5- a]pyrimidines.

Authors:  Gia L Hoang; Andrew D Streit; Jonathan A Ellman
Journal:  J Org Chem       Date:  2018-12-10       Impact factor: 4.354

6.  Synthesis of Azolo[1,3,5]triazines via Rhodium(III)-Catalyzed Annulation of N-Azolo Imines and Dioxazolones.

Authors:  Gia L Hoang; Kim Søholm Halskov; Jonathan A Ellman
Journal:  J Org Chem       Date:  2018-06-27       Impact factor: 4.354

7.  Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation.

Authors:  Matteo Faltracco; Verena Sukowski; Max van Druenen; Trevor A Hamlin; F Matthias Bickelhaupt; Eelco Ruijter
Journal:  J Org Chem       Date:  2020-07-13       Impact factor: 4.354

8.  Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII -Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls.

Authors:  Sun Dongbang; Zican Shen; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

9.  Convergent Synthesis of α-Branched Amines by Transition-Metal-Catalyzed C-H Bond Additions to Imines.

Authors:  Joshua R Hummel; Jonathan A Ellman
Journal:  Isr J Chem       Date:  2017-06-29       Impact factor: 3.333

10.  RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones via Annulation of N-Methoxyamides and Nitroalkenes.

Authors:  Tyler J Potter; Yuantao Li; Michael D Ward; Jonathan A Ellman
Journal:  European J Org Chem       Date:  2018-06-11
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