Literature DB >> 17458977

Cationic Rh(I)/modified-BINAP-catalyzed reactions of carbonyl compounds with 1,6-diynes leading to dienones and ortho-functionalized aryl ketones.

Ken Tanaka1, Yousuke Otake, Azusa Wada, Keiichi Noguchi, Masao Hirano.   

Abstract

We have determined that a cationic rhodium(I)/H8-BINAP complex catalyzes a [2 + 2 + 2] cycloaddition of both activated and unactivated carbonyl compounds with 1,6-diynes leading to dienones in high yields. On the other hand, unactivated aryl ketones react with 1,6-diynes in the presence of a cationic rhodium(I)/Segphos complex to give ortho-functionalized aryl ketones in high yields.

Entities:  

Year:  2007        PMID： 17458977     DOI： 10.1021/ol0707721

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


  6 in total

1.  C-H Activation by Isolable Cationic Bis(phosphine) Cobalt(III) Metallacycles.

Authors:  William G Whitehurst; Junho Kim; Stefan G Koenig; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2022-10-04       Impact factor: 16.383

2.  ESI-MS, DFT, and synthetic studies on the H(2)-mediated coupling of acetylene: insertion of C=X bonds into rhodacyclopentadienes and Brønsted acid cocatalyzed hydrogenolysis of organorhodium intermediates.

Authors:  Vanessa M Williams; Jong Rock Kong; Byoung Joon Ko; Yogita Mantri; Jennifer S Brodbelt; Mu-Hyun Baik; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-11-11       Impact factor: 15.419

Review 3.  Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

Authors:  Denise A Colby; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

4.  Three-Component Coupling of Arenes, Ethylene, and Alkynes Catalyzed by a Cationic Bis(phosphine) Cobalt Complex: Intercepting Metallacyclopentenes for C-H Functionalization.

Authors:  William G Whitehurst; Junho Kim; Stefan G Koenig; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2022-03-04       Impact factor: 15.419

Review 5.  Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C-N Axis via Enantioselective Catalysis.

Authors:  Xiao Xiao; Biao Chen; Yi-Ping Yao; Hai-Jie Zhou; Xu Wang; Neng-Zhong Wang; Fen-Er Chen
Journal:  Molecules       Date:  2022-10-04       Impact factor: 4.927

6.  Aromatic C-H addition of ketones to imines enabled by manganese catalysis.

Authors:  Bingwei Zhou; Yuanyuan Hu; Ting Liu; Congyang Wang
Journal:  Nat Commun       Date:  2017-10-27       Impact factor: 14.919
  6 in total

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