[1,2]- or [2,3]-Rearrangement of Onium Ylides of Allyl and Benzyl Ethers and Sulfides via in Situ-Generated Iodonium Ylides

2006 ◽  
Vol 8 (19) ◽  
pp. 4359-4361 ◽  
Author(s):  
Graham K. Murphy ◽  
F. G. West
Keyword(s):  
Benzyl Ethers ◽  
Iodonium Ylides

Benzylation of arenes with benzyl ethers promoted by the in situ prepared superacid BF3–H2O

2014 ◽  
Vol 16 (6) ◽  
pp. 2976 ◽  
Author(s):  
Yu Li ◽  
Yan Xiong ◽  
Xueming Li ◽  
Xuege Ling ◽  
Ruofeng Huang ◽  
...  
Keyword(s):  
Benzyl Ethers

Wittig Reagents as Metallocarbene Precursors: In Situ Generated Monocarbonyl Iodonium Ylides

2013 ◽  
Vol 2013 (29) ◽  
pp. 6540-6544 ◽  
Author(s):  
Phyllis E. Ho ◽  
Jason Tao ◽  
Graham K. Murphy
Keyword(s):  
Iodonium Ylides

scholarly journals Copper-Catalyzed Benzylic C–H Coupling with Alcohols via Radical Relay

2019 ◽  
Author(s):  
Huayou Hu ◽  
Si-Jie Chen ◽  
Shane Krska ◽  
Shannon Stahl
Keyword(s):  
Copper Catalyst ◽  
Three Dimensional ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Selective Functionalization ◽  
Modern Chemical ◽  
Benzyl Ethers ◽  
Site Selective

Cross coupling reactions enable rapid convergent synthesis of diverse molecules and provide the foundation for modern chemical synthesis. The most widely used methods employ sp2-hybridized coupling partners, such as aryl halides or related pre-functionalized substrates. Here, we demonstrate copper-catalyzed oxidative cross-coupling of benzylic C–H bonds with alcohols to afford benzyl ethers, enabled by mechanistic insights that led to a novel reductant-based strategy for in situ regeneration of the active copper catalyst. The reactions employ the C–H substrate as the limiting reagent and exhibit broad scope with respect to both substrate partners. This approach to direct site-selective functionalization of sp3 C–H bonds provides the basis for efficient three-dimensional diversification of organic molecules and should find widespread utility in organic synthesis, particularly for medicinal chemistry applications.

ChemInform Abstract: Wittig Reagents as Metallocarbene Precursors: In situ Generated Monocarbonyl Iodonium Ylides.

ChemInform ◽  
2014 ◽  
Vol 45 (10) ◽  
pp. no-no
Author(s):  
Phyllis E. Ho ◽  
Jason Tao ◽  
Graham K. Murphy
Keyword(s):  
Iodonium Ylides
Sign in / Sign up

Export Citation Format

Share Document