Oxime ethers as versatile precursors in organic synthesis: a review

RSC Advances ◽  
2015 ◽  
Vol 5 (97) ◽  
pp. 79361-79384 ◽  
Author(s):  
Zohreh Mirjafary ◽  
Morteza Abdoli ◽  
Hamid Saeidian ◽  
Sadjad Boroon ◽  
Ali Kakanejadifard
Keyword(s):  
Organic Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Metal Catalyzed

This review is a survey of the literature describing synthetic applications of oxime ethers. The cyclization and metal-catalyzed cross-coupling reactions of oxime ethers in recent years are also highlighted.

Microwave-assisted Carbon-carbon and Carbon-heteroatom Cross-coupling Reactions in Organic Synthesis

2020 ◽  
Vol 7 (2) ◽  
pp. 86-98
Author(s):  
Rammyani Pal ◽  
Chhanda Mukhopadhyay
Keyword(s):  
Microwave Irradiation ◽  
Organic Synthesis ◽  
Cross Coupling ◽  
Side Reactions ◽  
Coupling Reactions ◽  
Considerable Effort ◽  
Microwave Assisted ◽  
External Heat Source ◽  
Cross Coupling Reactions ◽  
Metal Catalyzed

Conventionally, the organic reactions are accomplished by conductive heating with an external heat source like an oil bath. On the contrary, since its inception, the application of microwave irradiation is growing as a suitable alternate heating method in organic synthesis. Microwave heating considerably reduces the reaction time without promoting any side reactions. The fundamental synthetic organic chemistry majorly deals with transition-metal-catalyzed C–C and C–heteroatom bond formation reactions. It is one of the most important methods in contemporary chemistry resulting in a tremendous increment in the applications of these reactions during the last few years. This field has been acknowledged with a number of Nobel Prizes during the last decade (2001, 2005 and 2010). A considerable effort has been done on the continuous development of new ligands and catalysts as well as an increased understanding of the mechanisms for the improvement of the reaction condition. This review focuses on some of the latest developments in the area of cross-coupling reactions aided by microwave irradiation.

scholarly journals Recent Advances in Metal-Catalyzed Alkyl–Boron (C(sp3)–C(sp2)) Suzuki-Miyaura Cross-Couplings

Catalysts ◽  
2020 ◽  
Vol 10 (3) ◽  
pp. 296 ◽  
Author(s):  
Janwa El-Maiss ◽  
Tharwat Mohy El Dine ◽  
Chung-Shin Lu ◽  
Iyad Karamé ◽  
Ali Kanj ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Significant Progress ◽  
Cross Coupling Reactions ◽  
Recent Advances ◽  
Boron Chemistry ◽  
Metal Catalyzed ◽  
Applied Fields

Boron chemistry has evolved to become one of the most diverse and applied fields in organic synthesis and catalysis. Various valuable reactions such as hydroborylations and Suzuki–Miyaura cross-couplings (SMCs) are now considered as indispensable methods in the synthetic toolbox of researchers in academia and industry. The development of novel sterically- and electronically-demanding C(sp3)–Boron reagents and their subsequent metal-catalyzed cross-couplings attracts strong attention and serves in turn to expedite the wheel of innovative applications of otherwise challenging organic adducts in different fields. This review describes the significant progress in the utilization of classical and novel C(sp3)–B reagents (9-BBN and 9-MeO-9-BBN, trifluoroboronates, alkylboranes, alkylboronic acids, MIDA, etc.) as coupling partners in challenging metal-catalyzed C(sp3)–C(sp2) cross-coupling reactions, such as B-alkyl SMCs after 2001.

Developments in Organocatalyzed C(Ar)- C(Ar) Bond formation Reactions via Single Electron Transfer Mechanism: An Overview

2021 ◽  
Vol 08 ◽  
Author(s):  
Lalit Yadav ◽  
Sandeep Chaudhary
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Metal Free ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: The formation of new bonds through C-C bond formation is of utmost importance in the synthesis of biologically privileged scaffolds and therapeutic drugs. In recent years, extensive efforts has been done to improve the intermolecular and intramolecular cross-coupling reaction in the simple, mild, efficient, economical, and eco-friendly manner via transition metal-free or organocatalytic direct C-H bond activation methodology. The traditional crosscoupling era continuously shifted to metal-free, organocatalytic, or metal-free cross-dehydrogenative coupling strategies to fast-track the reactions and diminishing the typical purification processes. Therefore, recent advances on the transitionmetal-free, organocatalytic inter- and intra-molecular cross-coupling reactions have been introduced and discussed in the present article. In view of the reaction mechanism, organocatalytic cross-coupling reactions undergo through the radical pathways, radical anionic intermediate which is completely different from traditional transition metal-catalyzed reactions. The exploration of transition metal-free organocatalyzed cross-couplings for direct C-H arylation of arenes has grown significantly, thereby, improving the formation of a wide range of aryl-aryl /aryl-heteroaryl/ heteroaryl-heteroaryl compounds. In the survey, transition metal-free/organocatalytic cross-coupling reactions showed a higher efficiency under simple and mild conditions than the comparative transition metal-catalyzed cross-coupling reactions. However, the higher regioselectivity and chemoselectivity are still far ahead in organocatalytic cross-coupling reactions due to their specific intrinsic mechanistic pathway. The tuning of many parameters such as oxidative states, ligands coordination, and counter anions, etc., which results in the specific direct C-H functionalization with flexible methodology are missing in the transition metal-free cross-coupling reactions. The highly systematic transition metal-catalyzed chemistry is still playing a dominant role over transition metal-free chemistry in organic synthesis. The organocatalyzed transition-metal-free conditions should be more efficient, chemoselective, and regioselective for further potential development and applications in organic synthesis. For the endless pursuit of sustainable chemistry and green chemistry, such transition-metalfree/organocatalytic reactions should be never ceased. Additional curious attention and interest have been developed so far, and chemists are showing their eagerness and talents to uncover the hidden treasure of green chemistry. In this review article, we highlighted the developments of various transition metal-free/organocatalytic C-H bond activation reactions which further encourages the advancement in the development of sustainable C-C coupling reactions and their further applications towards the synthesis of biologically privileged scaffolds and drug molecules.

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

Synthesis of Marine Polyacetylenes Callyberynes A−C by Transition-Metal-Catalyzed Cross-Coupling Reactions to sp Centers

2006 ◽  
Vol 71 (7) ◽  
pp. 2802-2810 ◽  
Author(s):  
Susana López ◽  
Francisco Fernández-Trillo ◽  
Pilar Midón ◽  
Luis Castedo ◽  
Carlos Saá
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Felipe C. Demidoff ◽  
Leandro L. de Carvalho ◽  
Eduardo José P. Rodrigues Filho ◽  
Andréa Luzia F. de Souza ◽  
Chaquip D. Netto
Keyword(s):  
Click Chemistry ◽  
Organic Synthesis ◽  
Biological Activities ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Large Array ◽  
Terminal Alkyne ◽  
Co Catalyst ◽  
Cross Coupling Reactions ◽  
Convenient Synthesis

AbstractFunctionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free CuI-mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.

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