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Literature DB >> 27385089

Synthesis and applications of rhodacyclopentanones derived from C-C bond activation.

Abstract

Rhodacyclopentanones, an "sp(3)-rich" class of metallacycle, underpin an emerging range of catalytic methodologies for the direct generation of complex scaffolds. This review highlights strategies for accessing rhodacyclopentanones (and related species) by C-C bond activation of cyclobutanones or cyclopropanes. The scope and mechanism of methodologies that exploit these activation modes is outlined.

Entities: Chemical

Year: 2016 PMID： 27385089 PMCID： PMC5010148 DOI： 10.1039/c6cc04359c

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

57 in total

1. Lactone Formation by Rhodium-Catalyzed C-C Bond Cleavage of Cyclobutanone We thank Dr. T. Tanaka (Kyoto University) for GC analysis of H(2), and Dr. M. Miura (Osaka University) for helpful discussions. Support from Monbusho (Grant-in-Aid for Scientific Research on Priority Areas, No. 283: Innovative Synthetic Reactions) is gratefully acknowledged.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-07-17 Impact factor: 15.336

2. Selective, catalytic carbon-carbon bond activation and functionalization promoted by late transition metal catalysts.

Authors: Suzanne C Bart; Paul J Chirik
Journal: J Am Chem Soc Date: 2003-01-29 Impact factor: 15.419

3. Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors: Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal: Chem Rev Date: 2007-07 Impact factor: 60.622

4. Three-component cycloadditions: the first transition metal-catalyzed [5+2+1] cycloaddition reactions.

Authors: Paul A Wender; Gabriel G Gamber; Robert D Hubbard; Lei Zhang
Journal: J Am Chem Soc Date: 2002-03-27 Impact factor: 15.419

5. Transition metal-catalyzed intermolecular [5+2] and [5+2+1] cycloadditions of allenes and vinylcyclopropanes.

Authors: Hermann A Wegner; Armin de Meijere; Paul A Wender
Journal: J Am Chem Soc Date: 2005-05-11 Impact factor: 15.419

6. The C-C bond activation and skeletal rearrangement of cycloalkanone imine by Rh(I) catalysts.

Authors: C H Jun; H Lee; S G Lim
Journal: J Am Chem Soc Date: 2001-01-31 Impact factor: 15.419

7. Nickel-catalyzed arylcyanation of alkynes.

Authors: Yoshiaki Nakao; Shinichi Oda; Tamejiro Hiyama
Journal: J Am Chem Soc Date: 2004-11-03 Impact factor: 15.419

8. Strain energy of small ring hydrocarbons. Influence of C-h bond dissociation energies.

Authors: Robert D Bach; Olga Dmitrenko
Journal: J Am Chem Soc Date: 2004-04-07 Impact factor: 15.419

9. Catalyzed intramolecular olefin insertion into a carbon-carbon single bond.

Authors: Masahiro Murakami; Tamon Itahashi; Yoshihiko Ito
Journal: J Am Chem Soc Date: 2002-11-27 Impact factor: 15.419

10. Ru- and Rh-catalyzed C-C bond cleavage of cyclobutenones: reconstructive and selective synthesis of 2-pyranones, cyclopentenes, and cyclohexenones.

Authors: Teruyuki Kondo; Yoshinori Taguchi; Yushi Kaneko; Masatsugu Niimi; Take-Aki Mitsudo
Journal: Angew Chem Int Ed Engl Date: 2004-10-11 Impact factor: 15.336

14 in total

1. Nickel-Catalyzed Chemo- and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles.

Authors: Xuan Zhou; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2016-11-04 Impact factor: 15.336

2. Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins.

Authors: Xuan Zhou; Haye Min Ko; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2016-10-06 Impact factor: 15.336

Review 3. Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Authors: Hiroki Sato; Ben W H Turnbull; Keisuke Fukaya; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2018-02-06 Impact factor: 15.336

4. "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Authors: Peng-Hao Chen; Brent A Billett; Tatsuhiro Tsukamoto; Guangbin Dong
Journal: ACS Catal Date: 2017-01-06 Impact factor: 13.084

5. Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors: Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal: J Am Chem Soc Date: 2018-07-11 Impact factor: 15.419

6. Recent Advances in the Development of Catalytic Methods that Construct Medium-ring Lactams, Partially Saturated Benzazepines and their Derivatives.

Authors: Wrickban Mazumdar; Tom G Driver
Journal: Synthesis (Stuttg) Date: 2021 Impact factor: 3.157

7. New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes.

Authors: Gang-Wei Wang; Niall G McCreanor; Megan H Shaw; William G Whittingham; John F Bower
Journal: J Am Chem Soc Date: 2016-10-06 Impact factor: 15.419