Mechanistic studies for dirhodium-catalyzed ring expansion reactions

文献情報

出版日 2017-02-09

DOI 10.1039/C6QO00713A

インパクトファクター 5.281

著者

Yin Wei, Xu-Bo Hu, Kai Chen

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要旨

The mechanisms for dirhodium-catalyzed ring expansion reactions of azide tethered methylenecyclopropanes and their analogues were systematically investigated by DFT calculations. The calculation results indicate that the dirhodium catalyst is essential for generating a reactive Rh2–nitrene intermediate having radical character; however, it is not essential for controlling final product selectivities. For substrates involving a three-membered ring, the experimentally obtained C–N bond formation product is a thermodynamically favored product. In contrast, for substrates having a larger ring, the kinetically favored product is the main product. The DFT calculations presented here account for previous experimental findings, and throw light on other dirhodium-catalyzed reactions involving nitrene or carbene intermediates.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Mechanistic studies for dirhodium-catalyzed ring expansion reactions

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