Dehydrogenative alcohol coupling and one-pot cross metathesis/dehydrogenative coupling reactions of alcohols using Hoveyda-Grubbs catalysts

2021 ◽  
Author(s):  
Halenur Özer ◽  
Dilan Arslan ◽  
Bengi Öztürk
Keyword(s):  
Coupling Reactions ◽  
One Pot ◽  
Ruthenium Hydride ◽  
Cross Metathesis ◽  
Dehydrogenative Coupling ◽  
Grubbs Catalysts

In this study, in-situ formed ruthenium hydride species that were generated from Grubbs type catalyst are used as efficient catalysts for dehydrogenative alcohol coupling and sequential cross-metathesis/dehydrogenative coupling reactions. The...

scholarly journals Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions

RSC Advances ◽  
2020 ◽  
Vol 10 (42) ◽  
pp. 24830-24839
Author(s):  
Xin Chen ◽  
Yunyun Bian ◽  
Baichuan Mo ◽  
Peng Sun ◽  
Chunxia Chen ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
One Pot ◽  
Dehydrogenative Coupling ◽  
Carboxylic Esters

One-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential oxidative Chan–Lam N-arylation and cross-dehydrogenative coupling (CDC) reaction.

ChemInform Abstract: One-Pot Negishi Cross-Coupling Reactions of in situ Generated Zinc Reagents with Aryl Chlorides, Bromides, and Triflates.

ChemInform ◽  
2009 ◽  
Vol 40 (5) ◽  
Author(s):  
Shohei Sase ◽  
Milica Jaric ◽  
Albrecht Metzger ◽  
Vladimir Malakhov ◽  
Paul Knochel
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions

scholarly journals Negishi coupling reactions with [11C]CH3I: a versatile method for efficient 11C–C bond formation

2018 ◽  
Vol 54 (35) ◽  
pp. 4398-4401 ◽  
Author(s):  
Luka Rejc ◽  
Vanessa Gómez-Vallejo ◽  
Jesús Alcázar ◽  
Nerea Alonso ◽  
José Ignacio Andrés ◽  
...  
Keyword(s):  
Bond Formation ◽  
Coupling Reactions ◽  
One Pot ◽  
Negishi Coupling

11C–C bonds can be rapidly formed by one-pot Negishi coupling between in situ-formed [11C]CH3ZnI and halides or triflates.

scholarly journals Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

2014 ◽  
Vol 10 ◽  
pp. 3031-3037 ◽  
Author(s):  
Kuppusamy Bharathimohan ◽  
Thanasekaran Ponpandian ◽  
A Jafar Ahamed ◽  
Nattamai Bhuvanesh
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Triazole Derivatives ◽  
One Pot Synthesis ◽  
Cross Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Herein, we describe a one-pot protocol for the synthesis of a novel series of polycyclic triazole derivatives. Transition metal-catalyzed decarboxylative CuAAC and dehydrogenative cross coupling reactions are combined in a single flask and achieved good yields of the respective triazoles (up to 97% yield). This methodology is more convenient to produce the complex polycyclic molecules in a simple way.

Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction

Synthesis ◽  
2019 ◽  
Vol 52 (01) ◽  
pp. 75-84 ◽  
Author(s):  
Peng Sun ◽  
Jiaojiao Yang ◽  
Zirui Song ◽  
Yichao Cai ◽  
Yajie Liu ◽  
...  
Keyword(s):  
Mixed Solvents ◽  
Coupling Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Dehydrogenative Coupling ◽  
High Yields

Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The initial hydroamination of anilines to ester arylpropiolates in benzene can proceed in a stereoselective manner to give ester (Z)-3-(arylamino)acrylates in the presence of CuCl2/phenanthroline, KMnO4, and KHCO3 at 120 °C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular oxidative alkenylation of aromatic C–H bond in mixed solvents (benzene/DMSO 1:1) at 130 °C affording multi-substituted­ indoles in good to high yields.

One-Pot Negishi Cross-Coupling Reactions of In Situ Generated Zinc Reagents with Aryl Chlorides, Bromides, and Triflates

2008 ◽  
Vol 73 (18) ◽  
pp. 7380-7382 ◽  
Author(s):  
Shohei Sase ◽  
Milica Jaric ◽  
Albrecht Metzger ◽  
Vladimir Malakhov ◽  
Paul Knochel
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions

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.).

scholarly journals Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry

2017 ◽  
Vol 12 (5) ◽  
pp. 1934578X1701200
Author(s):  
Silvia Roscales ◽  
Joaquín Plumet
Keyword(s):  
Diels Alder ◽  
Coupling Reactions ◽  
Alkyne Metathesis ◽  
Heck Reactions ◽  
One Pot ◽  
Cross Metathesis ◽  
Cross Coupling Reactions ◽  
Synthetic Procedure ◽  
Metathesis Reactions ◽  
Metal Catalyzed

Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Diels-Alder or Heck reactions, makes metathesis one of the most powerful and reliable synthetic procedure. In particular, Ring-Rearrangement Metathesis (RRM) refers to the combination of several metathesis transformations into a domino process such as ring-opening metathesis (ROM)/ring-closing metathesis (RCM) and ROM-cross metathesis (CM) in a one-pot operation. RRM delivers complex frameworks that are difficult to assemble by conventional methods constitutingan atom economic process. RRM is applicable to mono- and polycyclic systems of varying ring sizes such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, pyran systems, bicyclo[2.2.1]heptene derivatives, bicyclo[2.2.2]octene derivatives, bicyclo[3.2.1]octene derivatives and bicyclo[3.2.1]octene derivatives. In this review our attention has focused on the RRM reactions in 7-oxabicyclo[2.2.1]heptene derivatives and on their application in the synthesis of natural products or significant subunits of them.

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