Literature DB >> 30221007

Direct activation of relatively unstrained carbon-carbon bonds in homogeneous systems.

Alpay Dermenci1, Jotham W Coe1, Guangbin Dong2.   

Abstract

New modes of chemical reactivity are of high value to synthetic organic chemistry. In this vein, carbon-carbon (C-C) activation is an emerging field that offers new possibilities for synthesizing valuable complex molecules. This review discusses the pioneering stoichiometric discoveries in this field up to the most recent synthetic applications that apply catalytic transformations. Specifically, the review focuses on C-C activation in relatively unstrained systems, including stoichiometric reactions, chelation-directed and chelation-free catalytic reactions. While the field of C-C activation of relatively unstrained systems is underdeveloped, we expect that this review will provide insight into new developments and pave the path for robust, practical applications.

Entities:  

Year:  2014        PMID: 30221007      PMCID: PMC6136440          DOI: 10.1039/c4qo00053f

Source DB:  PubMed          Journal:  Org Chem Front        ISSN: 2052-4110            Impact factor:   5.281


  25 in total

1.  Direct exchange of a ketone methyl or aryl group to another aryl group through C-C bond activation assisted by rhodium chelation.

Authors:  Jingjing Wang; Weiqiang Chen; Sujing Zuo; Lu Liu; Xinrui Zhang; Jianhui Wang
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-04       Impact factor: 15.336

2.  Stable radicals during photodecarbonylations of trityl-alkyl ketones enable solid state reactions through primary and secondary radical centers.

Authors:  Gregory Kuzmanich; Arunkumar Natarajan; Yanhui Shi; Brian O Patrick; John R Scheffer; Miguel A Garcia-Garibay
Journal:  Photochem Photobiol Sci       Date:  2011-09-22       Impact factor: 3.982

3.  Rate-limiting step of the Rh-catalyzed carboacylation of alkenes: C-C bond activation or migratory insertion?

Authors:  J Patrick Lutz; Colin M Rathbun; Susan M Stevenson; Breanna M Powell; Timothy S Boman; Casey E Baxter; John M Zona; Jeffrey B Johnson
Journal:  J Am Chem Soc       Date:  2011-12-20       Impact factor: 15.419

4.  Pyridinyl directed alkenylation with olefins via Rh(III)-catalyzed C-C bond cleavage of secondary arylmethanols.

Authors:  Hu Li; Yang Li; Xi-Sha Zhang; Kang Chen; Xin Wang; Zhang-Jie Shi
Journal:  J Am Chem Soc       Date:  2011-09-13       Impact factor: 15.419

5.  Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters: synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement.

Authors:  Mieko Arisawa; Manabu Kuwajima; Fumihiko Toriyama; Guangzhe Li; Masahiko Yamaguchi
Journal:  Org Lett       Date:  2012-07-10       Impact factor: 6.005

6.  Catalysis of diazoalkane-carbonyl homologation. How new developments in hydrazone oxidation enable the carbon insertion strategy for synthesis.

Authors:  David C Moebius; Victor L Rendina; Jason S Kingsbury
Journal:  Top Curr Chem       Date:  2014

7.  Beta-aryl eliminations from Rh(I) iminyl complexes.

Authors:  Pinjing Zhao; John F Hartwig
Journal:  J Am Chem Soc       Date:  2005-08-24       Impact factor: 15.419

8.  Rh(I)-catalyzed decarbonylation of diynones via C-C activation: orthogonal synthesis of conjugated diynes.

Authors:  Alpay Dermenci; Rachel E Whittaker; Guangbin Dong
Journal:  Org Lett       Date:  2013-04-15       Impact factor: 6.005

9.  Carbon-carbon bond activation of 2,2,6,6-tetramethyl-piperidine-1-oxyl by a Rh(II) metalloradical: a combined experimental and theoretical study.

Authors:  Kin Shing Chan; Xin Zhu Li; Wojciech I Dzik; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2008-01-19       Impact factor: 15.419

10.  Catalytic deallylation of allyl- and diallylmalonates.

Authors:  David Necas; Matyás Turský; Martin Kotora
Journal:  J Am Chem Soc       Date:  2004-08-25       Impact factor: 15.419

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  16 in total

1.  Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature.

Authors:  Lin Deng; Yue Fu; Siu Yin Lee; Chengpeng Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2019-10-02       Impact factor: 15.419

2.  Coupling of sterically hindered trisubstituted olefins and benzocyclobutenones by C-C activation: total synthesis and structural revision of cycloinumakiol.

Authors:  Tao Xu; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-19       Impact factor: 15.336

3.  Activation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(II)-catalysed β-X elimination.

Authors:  Van T Tran; John A Gurak; Kin S Yang; Keary M Engle
Journal:  Nat Chem       Date:  2018-08-20       Impact factor: 24.427

4.  Distal-Bond-Selective C-C Activation of Ring-Fused Cyclopentanones: An Efficient Access to Spiroindanones.

Authors:  Ying Xia; Jianbo Wang; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-23       Impact factor: 15.336

Review 5.  Heterocycles from cyclopropenones.

Authors:  Ashraf A Aly; Alaa A Hassan; Sara M Mostafa; Asmaa H Mohamed; Esraa M Osman; AbdElAziz A Nayl
Journal:  RSC Adv       Date:  2022-06-24       Impact factor: 4.036

6.  Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones.

Authors:  Xukai Zhou; Yan Xu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2021-11-22       Impact factor: 16.383

7.  Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C-C Activation/Cycloaddition between Isatins and Isocyanates.

Authors:  Rong Zeng; Peng-Hao Chen; Guangbin Dong
Journal:  ACS Catal       Date:  2015-12-30       Impact factor: 13.084

8.  Controlled Rh-Catalyzed Mono- and Double-decarbonylation of Alkynyl α-Diones To Form Conjugated Ynones and Disubstituted Alkynes.

Authors:  Rachel E Whittaker; Guangbin Dong
Journal:  Org Lett       Date:  2015-10-27       Impact factor: 6.005

Review 9.  Challenges and opportunities for alkane functionalisation using molecular catalysts.

Authors:  Xinxin Tang; Xiangqing Jia; Zheng Huang
Journal:  Chem Sci       Date:  2017-11-09       Impact factor: 9.825

10.  Cobalt-catalyzed intramolecular decarbonylative coupling of acylindoles and diarylketones through the cleavage of C-C bonds.

Authors:  Tian-Yang Yu; Wen-Hua Xu; Hong Lu; Hao Wei
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825

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