Literature DB >> 23586742

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

Alpay Dermenci1, Rachel E Whittaker, Guangbin Dong.   

Abstract

Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

Entities:  

Year:  2013        PMID: 23586742     DOI: 10.1021/ol400815y

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

1.  Rhodium(I)-catalyzed decarbonylative spirocyclization through C-C bond cleavage of benzocyclobutenones: an efficient approach to functionalized spirocycles.

Authors:  Tao Xu; Nikolas A Savage; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-20       Impact factor: 15.336

2.  Nickel-catalyzed skeletal transformation of tropone derivatives via C-C bond activation: catalyst-controlled access to diverse ring systems.

Authors:  Takuya Kodama; Kanako Saito; Mamoru Tobisu
Journal:  Chem Sci       Date:  2022-04-04       Impact factor: 9.969

3.  Computational Study of Rh-Catalyzed Carboacylation of Olefins: Ligand-Promoted Rhodacycle Isomerization Enables Regioselective C-C Bond Functionalization of Benzocyclobutenones.

Authors:  Gang Lu; Cheng Fang; Tao Xu; Guangbin Dong; Peng Liu
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419

4.  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

5.  Cobalt-Catalyzed Intramolecular Alkyne/Benzocyclobutenone Coupling: C-C Bond Cleavage via a Tetrahedral Dicobalt Intermediate.

Authors:  Zixi Zhu; Xinghan Li; Sicong Chen; Peng-Hao Chen; Brent A Billett; Zhongxing Huang; Guangbin Dong
Journal:  ACS Catal       Date:  2017-12-22       Impact factor: 13.084

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

Authors:  Alpay Dermenci; Jotham W Coe; Guangbin Dong
Journal:  Org Chem Front       Date:  2014-03-27       Impact factor: 5.281

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

Authors:  Megan H Shaw; John F Bower
Journal:  Chem Commun (Camb)       Date:  2016-07-07       Impact factor: 6.222

8.  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

9.  Rh-Catalyzed Decarbonylation of Conjugated Ynones via Carbon-Alkyne Bond Activation: Reaction Scope and Mechanistic Exploration via DFT Calculations.

Authors:  Alpay Dermenci; Rachel E Whittaker; Yang Gao; Faben A Cruz; Zhi-Xiang Yu; Guangbin Dong
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825

  9 in total

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