scholarly journals Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics

2017 ◽  
Vol 8 (9) ◽  
pp. 5845-5888 ◽  
Author(s):  
Mahesh K. Lakshman ◽  
Prasanna K. Vuram
Keyword(s):  
Bond Formation ◽  
Coupling Reactions ◽  
Oxidative Amination ◽  
Dehydrogenative Coupling ◽  
Organic Catalysis

This is a perspective on cross-dehydrogenative coupling reactions of aromatic and heteroaromatic systems with ethers and alcohols via metal or organic catalysis, and through uncatalyzed means, leading to C–C and C–N bond formation.

scholarly journals Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2853-2866 ◽  
Author(s):  
Arkaitz Correa ◽  
Marcos Segundo
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Short Review ◽  
Great Promise ◽  
Coupling Reactions ◽  
Atom Economy ◽  
Bond Forming ◽  
Dehydrogenative Coupling ◽  
Peptide Derivatives

The functionalization of typically unreactive C(sp3)–H bonds holds great promise for reducing the reliance on existing functional groups while improving atom-economy and energy efficiency. As a result, this topic is a matter of genuine concern for scientists in order to achieve greener chemical processes. The site-specific modification of α-amino acid and peptides based upon C(sp3)–H functionalization still represents a great challenge of utmost synthetic importance. This short review summarizes the most recent advances in ‘Cross-Dehydrogenative Couplings’ of α-amino carbonyl compounds and peptide derivatives with a variety of nucleophilic coupling partners.1 Introduction2 C–C Bond-Forming Oxidative Couplings2.1 Reaction with Alkynes2.2 Reaction with Alkenes2.3 Reaction with (Hetero)arenes2.4 Reaction with Alkyl Reagents3 C–Heteroatom Bond-Forming Oxidative Couplings3.1 C–P Bond Formation3.2 C–N Bond Formation3.3 C–O and C–S Bond Formation4 Conclusions

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.).

Iron-Catalyzed Aerobic Oxidative Cross-Dehydrogenative C(sp3)–H/X–H (X = C, N, S) Coupling Reactions

Synlett ◽  
2020 ◽  
Vol 31 (18) ◽  
pp. 1753-1759
Author(s):  
Da-Zhen Xu ◽  
Ren-Ming Hu ◽  
Yi-Huan Lai
Keyword(s):  
Molecular Oxygen ◽  
Bond Formation ◽  
Research Topic ◽  
Synthetic Chemistry ◽  
Coupling Reactions ◽  
Iron Salts ◽  
Dehydrogenative Coupling ◽  
Recent Developments ◽  
Direct Functionalization ◽  
Made In

The direct functionalization of C(sp3)–H bonds is an attractive research topic in organic synthetic chemistry. The cross-dehydrogenative coupling (CDC) reaction provides a simple and powerful tool for the construction of C–C and C–heteroatom bonds. Recently, some progress has been made in the iron-catalyzed aerobic oxidative CDC reactions. Here, we present recent developments in the direct functionalization of C(sp3)–H bonds catalyzed by simple iron salts with molecular oxygen as the terminal oxidant.1 Introduction2 C(sp3)–C Bond Formation3 C(sp3)–N Bond Formation4 C(sp3)–S(Se) Bond Formation5 Conclusion and Outlook

scholarly journals Recent Advances in Transition-Metal-Catalyzed, Directed Aryl C–H/N–H Cross-Coupling Reactions

Synthesis ◽  
2017 ◽  
Vol 49 (20) ◽  
pp. 4586-4598 ◽  
Author(s):  
Martyn Henry ◽  
Mohamed Mostafa ◽  
Andrew Sutherland
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Short Review ◽  
Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Amination and amidation of aryl compounds using a transition-metal-catalyzed cross-coupling reaction typically involves prefunctionalization or preoxidation of either partner. In recent years, a new class of transition-metal-catalyzed cross-dehydrogenative coupling reaction has been developed for the direct formation of aryl C–N bonds. This short review highlights the substantial progress made for ortho-C–N bond formation via transition-metal-catalyzed chelation-directed aryl C–H activation and gives an overview of the challenges that remain for directed meta- and para-selective reactions.1 Introduction2 Intramolecular C–N Cross-Dehydrogenative Coupling2.1 Nitrogen Functionality as Both Coupling Partner and Directing Group2.2 Chelating-Group-Directed Intramolecular C–N Bond Formation3 Intermolecular C–N Cross-Dehydrogenative Coupling3.1 ortho-C–N Bond Formation3.1.1 Copper-Catalyzed Reactions3.1.2 Other Transition-Metal-Catalyzed Reactions3.2 meta- and para-C–N Bond Formation4 C–N Cross-Dehydrogenative Coupling of Acidic C–H Bonds5 Conclusions

scholarly journals Recent advances in sulfur–nitrogen bond formation via cross-dehydrogenative coupling reactions

RSC Advances ◽  
2018 ◽  
Vol 8 (33) ◽  
pp. 18456-18469 ◽  
Author(s):  
Fatemeh Alsadat Hosseini Nasab ◽  
Leila Zare Fekri ◽  
Aazam Monfared ◽  
Akram Hosseinian ◽  
Esmail Vessally
Keyword(s):  
Bond Formation ◽  
Coupling Reactions ◽  
Recent Advances ◽  
Dehydrogenative Coupling ◽  
Nitrogen Bonds ◽  
Nitrogen Bond

This review surveys the construction of sulfur–nitrogen bonds through cross-dehydrogenative coupling reactions between thiols and N–H compounds.

Transition-Metal-Free Synthetic Strategies for the Cross-Coupling Reactions in Water: A Green Approach

2020 ◽  
Vol 07 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Nilanjana Mukherjee
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Green Approach ◽  
Dehydrogenative Coupling

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.

Tunable Ligand Effects on Ruthenium Catalyst Activity for Selectively Preparing Imines or Amides by Dehydrogenative Coupling Reactions of Alcohols and Amines

2017 ◽  
Vol 23 (52) ◽  
pp. 12795-12804 ◽  
Author(s):  
Takafumi Higuchi ◽  
Risa Tagawa ◽  
Atsuhiro Iimuro ◽  
Shoko Akiyama ◽  
Haruki Nagae ◽  
...  
Keyword(s):  
Catalyst Activity ◽  
Ruthenium Catalyst ◽  
Coupling Reactions ◽  
Ligand Effects ◽  
Dehydrogenative Coupling
Sign in / Sign up

Export Citation Format

Share Document