Photochemical, Metal‐Free Sigmatropic Rearrangement Reactions of Sulfur Ylides

2019 ◽  
Vol 25 (27) ◽  
pp. 6703-6706 ◽  
Author(s):  
Zhen Yang ◽  
Yujing Guo ◽  
Rene M. Koenigs
Keyword(s):  
Sigmatropic Rearrangement ◽  
Sulfur Ylides ◽  
Metal Free ◽  
Rearrangement Reactions

Solvent-dependent, rhodium catalysed rearrangement reactions of sulfur ylides

2019 ◽  
Vol 55 (58) ◽  
pp. 8410-8413 ◽  
Author(s):  
Zhen Yang ◽  
Yujing Guo ◽  
Rene M. Koenigs
Keyword(s):  
Sigmatropic Rearrangement ◽  
Sulfur Ylides ◽  
Rearrangement Reactions

Depending on the solvent used, benzyl sulfides undergo in the presence of a rhodium(ii) catalyst either [1,2]- or [2,3]-sigmatropic rearrangement.

Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4348-4358 ◽  
Author(s):  
Fang Li ◽  
Feifei He ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Sigmatropic Rearrangement ◽  
Tertiary Amines ◽  
Amino Esters ◽  
Catalyst Free ◽  
Rearrangement Reaction ◽  
Rearrangement Reactions ◽  
Free Ammonium

The rearrangement reaction of ammonium ylides furnishes valuable α,α-disubstituted amino esters. In this work, we describe the visible-light photolysis reaction of aryldiazoacetates in the presence of tertiary amines that react via a free ammonium ylide in a sigmatropic rearrangement reaction to provide amino esters in moderate to very good yields (33 examples, up to 97% yield).

A Formal Metal-Free γ-Arylation of 1,3-Dicarbonyl Compounds via a Sequence of Isomerization/1,4-Addition/[3,3]-Sigmatropic Rearrangement

2021 ◽  
Author(s):  
Shi-Chao Lu ◽  
Fuqiang Wen ◽  
Xidong Guan
Keyword(s):  
Sigmatropic Rearrangement ◽  
Mechanistic Studies ◽  
Dicarbonyl Compounds ◽  
Metal Free

A metal-free redox arylation of alkynes with sulfoxides has been developed to provide an unconventional access to diverse γ-arylated 1,3-dicarbonyl compounds in an atom-economical manner. Mechanistic studies suggest that a...

Metal-free synthesis of biaryls from aryl sulfoxides and sulfonanilides via sigmatropic rearrangement

Tetrahedron ◽  
2020 ◽  
Vol 76 (51) ◽  
pp. 131232 ◽  
Author(s):  
Akira Yoshida ◽  
Koichi Okamoto ◽  
Tomoyuki Yanagi ◽  
Keisuke Nogi ◽  
Hideki Yorimitsu
Keyword(s):  
Sigmatropic Rearrangement ◽  
Metal Free

A New Class of Ammonium Ylid for [2,3]-Sigmatropic Rearrangement Reactions: ene-endo-Spiro Ylids

2005 ◽  
Vol 7 (10) ◽  
pp. 2075-2078 ◽  
Author(s):  
Edward Roberts ◽  
Julien P. Sançon ◽  
J. B. Sweeney
Keyword(s):  
Sigmatropic Rearrangement ◽  
New Class ◽  
Rearrangement Reactions

Regioselective [5,5]-Sigmatropic Rearrangement Reactions of Aryl Hydrazides

2006 ◽  
Vol 8 (10) ◽  
pp. 2047-2050 ◽  
Author(s):  
Hong-Min Kang ◽  
Young-Kwan Lim ◽  
In-Jee Shin ◽  
Hee-Yeon Kim ◽  
Cheon-Gyu Cho
Keyword(s):  
Sigmatropic Rearrangement ◽  
Rearrangement Reactions
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