Cleavage of C-C and C-O Bonds to Form C-C Bonds: Direct Cross-Coupling between Acetylenic Alcohols and Benzylic Carbonates

2018 ◽  
Vol 2018 (32) ◽  
pp. 4479-4482 ◽  
Author(s):  
Zhiyuan Mi ◽  
Jiahao Tang ◽  
Zhipeng Guan ◽  
Wei Shi ◽  
Hao Chen
Keyword(s):  
Cross Coupling ◽  
Direct Cross

ChemInform Abstract: Palladium-Catalyzed Direct Cross-Coupling Reaction Between Indenes and Electron-Deficient Alkenes.

ChemInform ◽  
2010 ◽  
Vol 41 (43) ◽  
pp. no-no
Author(s):  
Yun-He Xu ◽  
Wee-Jian Wang ◽  
Zhen-Kang Wen ◽  
Joshua Jonathan Hartley ◽  
Teck-Peng Loh
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Direct Cross ◽  
Palladium Catalyzed

ChemInform Abstract: Formal Direct Cross-Coupling of Phenols with Amines.

ChemInform ◽  
2016 ◽  
Vol 47 (15) ◽  
pp. no-no
Author(s):  
Zhengwang Chen ◽  
Huiying Zeng ◽  
Simon A. Girard ◽  
Feng Wang ◽  
Ning Chen ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Direct Cross

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me2SiHCl as both Reductant and Lewis Acid

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2425-2428 ◽  
Author(s):  
Bill Morandi ◽  
Yong Lee
Keyword(s):  
Functional Groups ◽  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Cross Coupling ◽  
Wide Range ◽  
Direct Cross ◽  
Sterically Hindered ◽  
Polar Functional Groups ◽  
Ether Synthesis ◽  
Dialkyl Ethers

We report that a Lewis acidic silane, Me2SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleo­philes.

scholarly journals Synthesis of 2-Alkenyl-Tethered Anilines

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2873-2888 ◽  
Author(s):  
Scott Denmark ◽  
Hyung Chi
Keyword(s):  
Lewis Acid ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Cope Rearrangement ◽  
The Third ◽  
Cross Metathesis ◽  
Direct Cross ◽  
Palladium Catalyzed

Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N-allylic anilines in the presence of a Lewis acid. The requisite N-allylic anilines were prepared by the addition of vinylmagnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C–N cross-coupling of aryl halides. Taken together, these three strategies allowed access to the requisite aniline substrates with pendant alkenes at the 2-position with excellent trans selectivities.

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