Catalytic Allylic Alkylation via the Cross-Dehydrogenative-Coupling Reaction between Allylic sp3C−H and Methylenic sp3C−H Bonds

2006 ◽  
Vol 128 (1) ◽  
pp. 56-57 ◽  
Author(s):  
Zhiping Li ◽  
Chao-Jun Li
Keyword(s):  
Coupling Reaction ◽  
Allylic Alkylation ◽  
Dehydrogenative Coupling ◽  
The Cross

The Cross‐Dehydrogenative Coupling Reaction of β‐Ketoesters with Quinoxalin‐2(1H)‐ones

2021 ◽  
Author(s):  
Hong-Yu Zhang ◽  
Zibing Yang ◽  
Huizhen Zhang ◽  
Ya-Ping Han ◽  
Jiquan Zhao ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Dehydrogenative Coupling ◽  
The Cross

scholarly journals Cross-dehydrogenative coupling for the intermolecular C–O bond formation

2015 ◽  
Vol 11 ◽  
pp. 92-146 ◽  
Author(s):  
Igor B Krylov ◽  
Vera A Vil’ ◽  
Alexander O Terent’ev
Keyword(s):  
Bond Formation ◽  
Coupling Reaction ◽  
Present Review ◽  
Published Data ◽  
Coupling Reactions ◽  
Sulfonic Acids ◽  
Dehydrogenative Coupling ◽  
Starting Compound ◽  
The Cross

The present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound, an oxygen atom of which is involved in the new bond, is called the OH-reagent or the O-reagent. Alcohols and carboxylic acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less often. The cross-dehydrogenative C–O coupling reactions are carried out using different C-reagents, such as compounds containing directing functional groups (amide, heteroaromatic, oxime, and so on) and compounds with activated C–H bonds (aldehydes, alcohols, ketones, ethers, amines, amides, compounds containing the benzyl, allyl, or propargyl moiety). An analysis of the published data showed that the principles at the basis of a particular cross-dehydrogenative C–O coupling reaction are dictated mainly by the nature of the C-reagent. Hence, in the present review the data are classified according to the structures of C-reagents, and, in the second place, according to the type of oxidative systems. Besides the typical cross-dehydrogenative coupling reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O2CR)2 reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.).

Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

2019 ◽  
Author(s):  
Tiantian Chen ◽  
Yang Yang ◽  
Liyu Xie ◽  
Haijian Yang ◽  
Guangbin Dong ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dual Role ◽  
Allylic Alkylation ◽  
Cross Coupling Reaction ◽  
Neutral Conditions

<p>We report a Ni(0)-catalyzed cross coupling reaction between simple ketones and 1,3-dienes. A variety of a-allylic alkylation products were formed in an 1,2-addition manner with excellent regioselectivity. Water was found to significantly accelerate this transformation. A HO-Ni-H species generated from oxidative addition of Ni(0) to H<sub>2</sub>O is proposed to play a “dual role” in activating both the ketone and the diene substrate.</p>

scholarly journals Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction

RSC Advances ◽  
2021 ◽  
Vol 11 (14) ◽  
pp. 8051-8054
Author(s):  
Rongxiang Chen ◽  
Bing Liu ◽  
Wenbo Li ◽  
Kai-Kai Wang ◽  
Changqing Miao ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Dehydrogenative Coupling ◽  
Aryl Ketones ◽  
High Yields

A cross dehydrogenative coupling reaction of aryl ketones with N-hydroxyphthalimide was realized. The reactions afforded a clean and facile access to diverse N-alkoxyphthalimide derivatives in high yields (up to 99%).

Hydroxymethylation of quinolines via iron promoted oxidative C–H functionalization: synthesis of arsindoline-A and its derivatives

2021 ◽  
Author(s):  
Bangarigalla Shantharjun ◽  
Damera Vani ◽  
Ramanjaneyulu Unnava ◽  
Mummadi Sandeep ◽  
Kallu Rajender Reddy
Keyword(s):  
Coupling Reaction ◽  
Dehydrogenative Coupling

Herein, we report a mild and efficient hydroxymethylation of quinolines via an iron promoted cross-dehydrogenative coupling reaction under external acid free conditions.

Topology Selectivity in On-Surface Dehydrogenative Coupling Reaction: Dendritic Structure versus Porous Graphene Nanoribbon

ACS Nano ◽  
2021 ◽  
Vol 15 (3) ◽  
pp. 4617-4626
Author(s):  
Jianmin Huang ◽  
Yu Pan ◽  
Tao Wang ◽  
Shengsheng Cui ◽  
Lin Feng ◽  
...  
Keyword(s):  
Dendritic Structure ◽  
Coupling Reaction ◽  
Graphene Nanoribbon ◽  
Porous Graphene ◽  
Dehydrogenative Coupling ◽  
Structure Versus
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