Literature DB >> 24512084

Formal carbene insertion into C-C bond: Rh(I)-catalyzed reaction of benzocyclobutenols with diazoesters.

Ying Xia1, Zhenxing Liu, Zhen Liu, Rui Ge, Fei Ye, Mohammad Hossain, Yan Zhang, Jianbo Wang.   

Abstract

A Rh(I)-catalyzed formal carbene insertion into C-C bond of benzocyclobutenols has been realized by employing diazoesters as carbene precursors. The product indanol derivatives were obtained in good yields and in diastereoselective manner under mild reaction conditions. All-carbon quaternary center is constructed at the carbenic carbon. This catalytic reaction involves selective cleavage of C-C bond, Rh(I) carbene insertion, and intramolecular aldol reaction.

Entities:  

Year:  2014        PMID： 24512084     DOI： 10.1021/ja500118w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  12 in total

1.  Rhodium-Catalyzed (4+1) Cycloaddition between Benzocyclobutenones and Styrene-Type Alkenes.

Authors:  Shusuke Ochi; Zining Zhang; Ying Xia; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-30       Impact factor: 16.823

Review 2.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

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.  (4+1) vs (4+2): Catalytic Intramolecular Coupling between Cyclobutanones and Trisubstituted Allenes via C-C Activation.

Authors:  Xuan Zhou; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2015-10-16       Impact factor: 15.419

5.  Rh-catalyzed Reagent-Free Ring Expansion of Cyclobutenones and Benzocyclobutenones.

Authors:  Peng-Hao Chen; Joshua Sieber; Chris H Senanayake; Guangbin Dong
Journal:  Chem Sci       Date:  2015-07-10       Impact factor: 9.825

6.  Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C-C bond cleavage: efficient access to trans-bicyclic compounds.

Authors:  Xinxin Zheng; Rui Guo; Guozhu Zhang; Dayong Zhang
Journal:  Chem Sci       Date:  2018-01-08       Impact factor: 9.825

7.  CO/O2 assisted oxidative carbon-carbon and carbon-heteroatom bond cleavage for the synthesis of oxosulfonates from DMSO and olefins.

Authors:  Ailong Shao; Meng Gao; Songtao Chen; Tao Wang; Aiwen Lei
Journal:  Chem Sci       Date:  2016-12-07       Impact factor: 9.825

8.  Aminofluorination: transition-metal-free N-F bond insertion into diazocarbonyl compounds.

Authors:  Gui Chen; Jinshuai Song; Yinghua Yu; Xuesong Luo; Chunsen Li; Xueliang Huang
Journal:  Chem Sci       Date:  2015-12-14       Impact factor: 9.825

9.  Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage.

Authors:  Rui Guo; Xinxin Zheng; Dayong Zhang; Guozhu Zhang
Journal:  Chem Sci       Date:  2017-01-23       Impact factor: 9.825

10.  Silver-Catalyzed Regio- and Stereoselective Formal Carbene Insertion into Unstrained C-C σ-Bonds of 1,3-Dicarbonyls.

Authors:  Zhaohong Liu; Xinyu Zhang; Matteo Virelli; Giuseppe Zanoni; Edward A Anderson; Xihe Bi
Journal:  iScience       Date:  2018-09-18
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