Mechanistic understanding of [Rh(NHC)]-catalyzed intramolecular [5 + 2] cycloadditions of vinyloxiranes and vinylcyclopropanes with alkynes-Reference-Cited by-同舟云学术

Mechanistic understanding of [Rh(NHC)]-catalyzed intramolecular [5 + 2] cycloadditions of vinyloxiranes and vinylcyclopropanes with alkynes

Published:2018 Issue:23 Volume:16 Page:4295-4303
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Zhou Huan¹²³⁴⁵,Wu Botao¹²³⁴⁵,Ma Jun-An¹²³⁴⁵,Dang Yanfeng¹²³⁴⁵^ORCID

Affiliation:

1. Department of Chemistry

2. Tianjin Key Laboratory of Molecular Optoelectronic Sciences

3. Tianjin University

4. and Collaborative Innovation Center of Chemical Science and Engineering

5. Tianjin 300072

Abstract

Rh-catalyzed hetero-[5 + 2] cycloaddition of vinyloxirane with alkyne occurs via oxidative alkyne–alkene cyclization, oxirane cleavage and reductive elimination, the first example where oxidative alkyne–alkene cyclization mechanism is preferred within Rh-catalyzed [5 + 2] cycloadditions.

Funder

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2018/OB/C8OB01117F

Reference106 articles.

1. Transition Metal-Mediated Cycloaddition Reactions

2. Transition Metal-Catalyzed Carbocyclizations in Organic Synthesis

3. Metal-Mediated Synthesis of Medium-Sized Rings