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Li XG, Sun M, Jin Q, et al. Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds. J Org Chem. 2016;81(9):3901-10doi: 10.1021/acs.joc.6b00264.
Li, X. G., Sun, M., Jin, Q., Liu, K., & Liu, P. N. (2016). Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds. The Journal of organic chemistry, 81(9), 3901-10. https://doi.org/10.1021/acs.joc.6b00264
Li, Xing Guang, et al. "Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds." The Journal of organic chemistry vol. 81,9 (2016): 3901-10. doi: https://doi.org/10.1021/acs.joc.6b00264
Li XG, Sun M, Jin Q, Liu K, Liu PN. Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds. J Org Chem. 2016 May 06;81(9):3901-10. doi: 10.1021/acs.joc.6b00264. Epub 2016 Apr 13. PMID: 27042947.
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J Org Chem. 2016 May 06;81(9):3901-10. doi: 10.1021/acs.joc.6b00264. Epub 2016 Apr 13.

Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds.

The Journal of organic chemistry

Xing Guang Li, Min Sun, Qiao Jin, Kai Liu, Pei Nian Liu

Affiliations

  1. Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China.

PMID: 27042947 DOI: 10.1021/acs.joc.6b00264

Abstract

A Rh(III)-catalyzed coupling/cyclization cascade reaction is described, which involves arylimidates and diazo compounds and proceeds via intermolecular C-C bond formation and subsequent intramolecular C-N bond formation. Mechanistic investigation revealed that the reaction is a two-step process: the initial Rh(III)-catalyzed coupling/cyclization proceeds very fast and the following dehydration is rather slow. The reaction provides a direct approach to isoquinolines and isoquinolin-3-ols without any oxidants.

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