Highly regioselective α-formylation and α-acylation of BODIPY dyes via tandem cross-dehydrogenative coupling with in situ deprotection

2019 ◽  
Vol 17 (20) ◽  
pp. 5121-5128 ◽  
Author(s):  
Fan Lv ◽  
Yang Yu ◽  
Erhong Hao ◽  
Changjiang Yu ◽  
Hua Wang ◽  
...  
Keyword(s):  
Dehydrogenative Coupling

An efficient protocol for the regioselective C–H α-formylation and α-acylation of BODIPY dyes using dioxolane derivatives as aldehyde equivalents is reported.

scholarly journals A cross-dehydrogenative C(sp3)−H heteroarylation via photo-induced catalytic chlorine radical generation

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Chia-Yu Huang ◽  
Jianbin Li ◽  
Chao-Jun Li
Keyword(s):  
Hydrogen Atom ◽  
Hydrogen Evolution ◽  
Alkyl Radical ◽  
Cobalt Catalyst ◽  
Alkylation Reaction ◽  
Hydrogen Atom Abstraction ◽  
Dehydrogenative Coupling ◽  
Radical Generation ◽  
Limited Scope

AbstractHydrogen atom abstraction (HAT) from C(sp3)–H bonds of naturally abundant alkanes for alkyl radical generation represents a promising yet underexplored strategy in the alkylation reaction designs since involving stoichiometric oxidants, excessive alkane loading, and limited scope are common drawbacks. Here we report a photo-induced and chemical oxidant-free cross-dehydrogenative coupling (CDC) between alkanes and heteroarenes using catalytic chloride and cobalt catalyst. Couplings of strong C(sp3)–H bond-containing substrates and complex heteroarenes, have been achieved with satisfactory yields. This dual catalytic platform features the in situ engendered chlorine radical for alkyl radical generation and exploits the cobaloxime catalyst to enable the hydrogen evolution for catalytic turnover. The practical value of this protocol was demonstrated by the gram-scale synthesis of alkylated heteroarene with merely 3 equiv. alkane loading.

Heterogeneous-Gold-Catalyzed Acceptorless Cross-Dehydrogenative Coupling of Hydrosilanes and Isocyanic Acid Generated in situ from Urea

2013 ◽  
Vol 125 (32) ◽  
pp. 8578-8581 ◽  
Author(s):  
Kento Taniguchi ◽  
Shintaro Itagaki ◽  
Kazuya Yamaguchi ◽  
Noritaka Mizuno
Keyword(s):  
Isocyanic Acid ◽  
Dehydrogenative Coupling

Photoredox Mediated Asymmetric Cross-Dehydrogenative Coupling of Enones and Tertiary Amines by Chiral Primary Amine Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zongbin Jia ◽  
Qi Yang ◽  
Sanzhong Luo
Keyword(s):  
Primary Amine ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Tertiary Amines ◽  
Dehydrogenative Coupling ◽  
Cross Coupling Reaction ◽  
Iminium Ion ◽  
Amine Catalysis ◽  
Catalytic Asymmetric

We report herein a catalytic asymmetric dehydrogenative cross-coupling reaction between enones and tertiary amines enabled by synergistic photoredox and chiral primary amine catalysis. The reaction was proposed to proceed via the interception of iminium ion intermediate, in situ generated from photoredox oxidation, by dienamine at α-position, following by isomerization, leading to aza-Morita-Baylis-Hillman-type products with good diastereo- and enantio- selectivity.

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.

ChemInform Abstract: Heterogeneous-Gold-Catalyzed Acceptorless Cross-Dehydrogenative Coupling of Hydrosilanes and Isocyanic Acid Generated in situ from Urea.

ChemInform ◽  
2013 ◽  
Vol 45 (1) ◽  
pp. no-no
Author(s):  
Kento Taniguchi ◽  
Shintaro Itagaki ◽  
Kazuya Yamaguchi ◽  
Noritaka Mizuno
Keyword(s):  
Isocyanic Acid ◽  
Dehydrogenative Coupling

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...

Ag(I)-Mediated In situ Dehydrogenative Coupling of 3-Amino-1,2,4-triazole into 3,3′-Azobis(1,2,4-triazole) in Cd(II) Coordination Polymers

2009 ◽  
Vol 48 (23) ◽  
pp. 10859-10861 ◽  
Author(s):  
Pei-Xiu Yin ◽  
Jian-Kai Cheng ◽  
Zhao-Ji Li ◽  
Lei Zhang ◽  
Ye-Yan Qin ◽  
...  
Keyword(s):  
Coordination Polymers ◽  
Dehydrogenative Coupling

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.).

Polystyrene trimethyl ammonium chloride impregnated Rh(0) (Rh@PMe3NCl) as a catalyst and methylating agent for esterification of alcohols through selective oxidation of methanol

2015 ◽  
Vol 5 (5) ◽  
pp. 2575-2580 ◽  
Author(s):  
Nitul Ranjan Guha ◽  
Dhananjay Bhattacherjee ◽  
Pralay Das
Keyword(s):  
Selective Oxidation ◽  
Ammonium Chloride ◽  
Trimethyl Ammonium Chloride ◽  
Ester Synthesis ◽  
Acetate Ester ◽  
Oxidation Of Methanol ◽  
Dehydrogenative Coupling

Rh@PMe3NCl acts as a cross-dehydrogenative coupling-methylating agent for the selective oxidation of methanol and it's in situ reaction with benzyl/alkyl alcohols for acetate ester synthesis is presented.

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