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Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides

1,2, 1,2, 1,2, 1,2,* and 1,2,*
1
State Key Laboratory of Drug Research and CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
2
University of Chinese Academy of Sciences, No.19A Yuquan Road, Beijing 100049, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Il Kim
Molecules 2019, 24(10), 1884; https://doi.org/10.3390/molecules24101884
Received: 28 April 2019 / Revised: 14 May 2019 / Accepted: 14 May 2019 / Published: 16 May 2019
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Abstract

A convenient Rh(III)-catalyzed C-H activation and cascade [4+2] annulation for the synthesis of naphthalenone sulfoxonium ylides has been developed. This method features perfect regioselectivity, mild and redox-neutral reaction conditions, and broad substrate tolerance with good to excellent yields. Preliminary mechanistic experiments were conducted and a plausible reaction mechanism was proposed. The new type naphthalenone sulfoxonium ylides could be further transformed into multi-substituted naphthols, which demonstrates the practical utility of this methodology. View Full-Text
Keywords: rhodium(III); sulfoxonium ylides; naphthols rhodium(III); sulfoxonium ylides; naphthols
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Song, X.; Han, X.; Zhang, R.; Liu, H.; Wang, J. Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides. Molecules 2019, 24, 1884.

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