Concepedia

Direct and metal-free arylsulfonylation of alkynes with sulfonylhydrazides for the construction of 3-sulfonated coumarins

Wei Wei, Jiangwei Wen, Daoshan Yang, Mengyuan Guo, Yingying Wang, Jinmao You, Hua Wang

Chemical Communications · 2014 · 192 citations · 45 references

DOI

Concepts

Abstract

A novel and metal-free procedure has been developed for the construction of 3-sulfonated coumarins via the direct difunctionalization of alkynoates with sulfonylhydrazides. The present protocol, which simply utilizes TBAI as the catalyst and TBHP as the oxidant, provides a convenient and highly efficient approach to construct a series of sulfonated coumarins with high regioselectivity and good functional group tolerance.

References

45

Dioxygen-Triggered Oxidative Radical Reaction: Direct Aerobic Difunctionalization of Terminal Alkynes toward β-Keto Sulfones

Qingquan Lu, Jian Zhang, Ganglu Zhao et al. · Journal of the American Chemical Society · 2013 · 491 citations

, , +12

A powerful combination: recent achievements on using TBAI and TBHP as oxidation system

Xiao‐Feng Wu, Jinlong Gong, Xinxin Qi · Organic & Biomolecular Chemistry · 2014 · 332 citations

, , +15

Copper-catalyzed direct oxysulfonylation of alkenes with dioxygen and sulfonylhydrazides leading to β-ketosulfones

Wei Wei, Chunli Liu, Daoshan Yang et al. · Chemical Communications · 2013 · 265 citations

, , +13

Palladium‐Catalyzed Three‐Component Diaryl Sulfone Synthesis Exploiting the Sulfur Dioxide Surrogate DABSO

Edward J. Emmett, Barry R. Hayter, Michael C. Willis · Angewandte Chemie International Edition · 2013 · 252 citations · Full text

, , +15

Tetrabutylammonium iodide catalyzed allylic sulfonylation of α-methyl styrene derivatives with sulfonylhydrazides

Xiaoqing Li, Xiangsheng Xu, Can Zhou · Chemical Communications · 2012 · 223 citations

, , +2