Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones

Run Sun¹, Yu Jiang¹, Xiang-Ying Tang², Min Shi^{3

4}

Affiliations

¹ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. siocxiangying@mail.sioc.ac.cn.
³ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China. mshi@mail.sioc.ac.cn.
⁴ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. mshi@mail.sioc.ac.cn.

PMID: 26934455
DOI: 10.1002/chem.201504914

Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones

Run Sun et al. Chemistry. 2016.

. 2016 Apr 11;22(16):5727-33.

doi: 10.1002/chem.201504914. Epub 2016 Mar 2.

Authors

Run Sun¹, Yu Jiang¹, Xiang-Ying Tang², Min Shi^{3

4}

Affiliations

¹ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. siocxiangying@mail.sioc.ac.cn.
³ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China. mshi@mail.sioc.ac.cn.
⁴ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. mshi@mail.sioc.ac.cn.

PMID: 26934455
DOI: 10.1002/chem.201504914

Abstract

New rhodium(II)-catalyzed or thermally induced intramolecular alkoxy group migration of N-sulfonyl-1,2,3-triazoles has been developed, affording divergent synthesis of 1,2-dihydroisoquinoline and 1-indanone derivatives according to different conditions. N-Sulfonyl keteneimine is the key intermediate for the synthesis of dihydroisoquinoline, whereas the aza-vinyl carbene intermediate results in the formation of 1-indanone.

Keywords: carbenes; heterocycles; rearrangement; rhodium; triazoles.

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Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones

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Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones

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