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Papers by tubai ghosh
Benign-Metal-Catalyzed Carbon–Carbon and Carbon–Heteroatom Bond Formation
Synlett
Carbon–carbon and carbon–heteroatom bond-formation reactions catalyzed by benign and inexpensive ... more Carbon–carbon and carbon–heteroatom bond-formation reactions catalyzed by benign and inexpensive metals are of much interest in organic synthesis, as these reactions provide green and cost-effective routes. This account summarizes our recent contributions to the construction of carbon–carbon and carbon–heteroatom bonds by using benign-metal catalysts. A number of carbon–heteroatom bond formations, including C–N, C–O, C–S, C–Se, C–Te, and C–P bond formations, are discussed. Mechanistic insights into several reactions are also reported1 Introduction2 C–C Bond Formation3 C–N and C–O Bond Formation4 Carbon–Chalcogen (C–S, C–Se, C–Te) and C–P Bond Formation5 Conclusions
Chapter 1 Magnetic metal nanoparticle-catalyzed carbon-heteroatom bond formation and synthesis of related heterocycles
Synthetic Applications
CCDC 1849955: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
CCDC 1849783: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
CCDC 1812296: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
1. Synthesis of Organoselenides by Coupling Reaction and C–H Activation – Recent Advances
Organoselenium Chemistry, 2020
Selenophenes
Comprehensive Heterocyclic Chemistry IV, 2022
Chemistry Teacher International, 2021
We have highlighted an example of a natural process like photosynthesis to introduce the subject ... more We have highlighted an example of a natural process like photosynthesis to introduce the subject of Green Chemistry. Photosynthesis can be an ideal example to illustrate a green process explaining all the features such as selection of raw materials, solvent, catalyst, energy, etc. for an environment-friendly reaction. From the same reaction, all the principles of Green Chemistry can be derived in a simpler way without the need of memorizing these in a set language. In this article, a few examples of green procedures for the synthesis of useful molecules have been illustrated in light of the knowledge of photosynthesis. The visible-light mediated reactions, organic reactions in water, and solvent-free organic reactions are discussed here for a practical illustration of Green synthesis.
Recent advances in the synthesis of bioactive five- and six-membered heterocycles catalyzed by heterogeneous metal catalysts
Green Synthetic Approaches for Biologically Relevant Heterocycles, 2021
Abstract The use of heterogeneous metal catalysts has received much interest for its primary adva... more Abstract The use of heterogeneous metal catalysts has received much interest for its primary advantages of ease of operation, easy recovery, and recyclability of catalysts. These features are of much significance in the context of green synthesis and applications in industry. This chapter highlights the recent progress in the synthesis of various five- and six-membered N-, O-, S-containing heterocycles utilizing a variety of heterogeneous-supported metal catalysts. These include pyrroles, pyrrolidines, indolizines, imidazoles, benzimidazoles, triazoles, pyridines and dihydropyridines, pyridinones, pyrimidines, pyrimidinones, benzofurans, furocoumarins, pyrans, chromenes, and a few fused heterocycles. The scopes and limitations of the procedures have been reported. The possible reaction pathways of several reactions are discussed for better understanding.
ChemistrySelect, 2018
An efficient C(sp2)-N cross coupling of cyclic and acyclic amides with styrenyl/aryl/heteroaryl h... more An efficient C(sp2)-N cross coupling of cyclic and acyclic amides with styrenyl/aryl/heteroaryl halides catalyzed by cobalt acetylacetonate in combination with copper(I) iodide, has been achieved. A library of diversely substituted cyclic and acyclic enamides have been obtained in high yields by this procedure. The reaction is stereoselective producing (E)-enamides from trans-styrenyl halides and (Z)-products from cis-halides. This procedure has been successfully employed for the coupling of other N-heterocycles such as pyrazole, imidazole and triazole with aryl/styrenyl/heteroaryl halides to produce the corresponding N-coupled products. A probable mechanism has been suggested.
ChemistrySelect, 2020
A convenient method has been developed for the synthesis of biarenyl chalcogenides through the in... more A convenient method has been developed for the synthesis of biarenyl chalcogenides through the interaction of bicyclic arenes and diaryl dichalcogenides on the surface of basic alumina under ball milling without any metal catalyst or solvent. This methodology shows wide substrate scope and is of high potential in organic synthesis due to its green aspects of ease of operation, shorter reaction time, ambient conditions and high yields.
Copper catalyzed cyanation through CC bond cleavage of gem-aryl dibromide followed by second cyanation of iodoarene by a released CN unit
Organic Chemistry Frontiers, 2018
A new approach for the synthesis of aryl cyanides through CC cleavage of styrenyl gem-dibromide ... more A new approach for the synthesis of aryl cyanides through CC cleavage of styrenyl gem-dibromide has been achieved.
The Journal of Organic Chemistry, 2018
An efficient method for the C(sp 2)-amidation of 8-aminoquinoline benzamide by acyl azide in the ... more An efficient method for the C(sp 2)-amidation of 8-aminoquinoline benzamide by acyl azide in the presence of copper acetate has been achieved via C-H activation. Interestingly, the loading of copper acetate has strong influence on the outcome of the reaction. The use of one equivalent of copper acetate produces the corresponding aroyl amide, whereas, the use of two equivalents led to acetyl amide. A series of substituted benzoyl and acetyl amides have been obtained. Cu(OAc)2.H2O K2CO3 CH3CN 2 Cu(OAc)2.H2O K2CO3 DCE-3 Cu(OAc)2.H2O K2CO3 DMF 17 4 Cu(OAc)2.H2O K2CO3 DMSO 71 5 Cu(OAc)2.H2O K2CO3 Toluene-6 Cu(OAc)2.H2O K2CO3 MeOH-7 Cu(OAc)2.H2O K2CO3 H2O 19 8 Cu(OAc)2.H2O Cs2CO3 DMSO-9 Cu(OAc)2.H2O NaOAC DMSO 20 10 Cu(OAc)2.H2O Na2CO3 DMSO 29 11 Cu(OAc)2.H2O Et3N DMSO trace 12 Cu(OAc)2.H2O K3PO4 DMSO 17 20 c Cu(OAc)2.H2O K2CO3 DMSO 15 21 Co(OAc)2 K2CO3 DMSO-22 Ni(OAc)2 K2CO3 DMSO trace 23 d Cu(OAc)2.H2O K2CO3 DMSO 61 24 e Cu(OAc)2.H2O K2CO3 DMSO 69
Visible Light Photocatalyzed Carbon-Heteroatom Bond Formation and Synthesis of Related Compounds
Current Green Chemistry, 2017
New Journal of Chemistry, 2016
An efficient C(sp2)–P cross coupling has been achieved using a Co/Cu catalytic system for access ... more An efficient C(sp2)–P cross coupling has been achieved using a Co/Cu catalytic system for access to vinyl and aryl phosphonates.
Arkivoc, 2019
The inert C-H bond functionalization via bond activation in the presence of transition metals usi... more The inert C-H bond functionalization via bond activation in the presence of transition metals using ball milling is reviewed. The use of several transition metals, such as Pd, Rh, Ru, Co, and Ir are covered in this review for a variety of important functionalizations, including halogenation, amidation, alkynylation, and dehydrogenative coupling, among others. These reactions are performed under mild conditions, usually without any solvent, and in relatively short reaction times.
Organic letters, Feb 16, 2018
A cobalt-catalyzed selective remote C-4 alkylation of 8-aminoquinoline amides via C-H activation ... more A cobalt-catalyzed selective remote C-4 alkylation of 8-aminoquinoline amides via C-H activation under irradiation with a CFL lamp in the presence of eosin Y at room temperature has been achieved. A series of pharmaceutically important C-4 quinoline amide-substituted ether derivatives has been obtained by this procedure. The C-4 functionalization of quinoline amides with inert ether is of much significance and was not reported earlier.
Benign-Metal-Catalyzed Carbon–Carbon and Carbon–Heteroatom Bond Formation
Synlett
Carbon–carbon and carbon–heteroatom bond-formation reactions catalyzed by benign and inexpensive ... more Carbon–carbon and carbon–heteroatom bond-formation reactions catalyzed by benign and inexpensive metals are of much interest in organic synthesis, as these reactions provide green and cost-effective routes. This account summarizes our recent contributions to the construction of carbon–carbon and carbon–heteroatom bonds by using benign-metal catalysts. A number of carbon–heteroatom bond formations, including C–N, C–O, C–S, C–Se, C–Te, and C–P bond formations, are discussed. Mechanistic insights into several reactions are also reported1 Introduction2 C–C Bond Formation3 C–N and C–O Bond Formation4 Carbon–Chalcogen (C–S, C–Se, C–Te) and C–P Bond Formation5 Conclusions
Chapter 1 Magnetic metal nanoparticle-catalyzed carbon-heteroatom bond formation and synthesis of related heterocycles
Synthetic Applications
CCDC 1849955: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
CCDC 1849783: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
CCDC 1812296: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
1. Synthesis of Organoselenides by Coupling Reaction and C–H Activation – Recent Advances
Organoselenium Chemistry, 2020
Selenophenes
Comprehensive Heterocyclic Chemistry IV, 2022
Chemistry Teacher International, 2021
We have highlighted an example of a natural process like photosynthesis to introduce the subject ... more We have highlighted an example of a natural process like photosynthesis to introduce the subject of Green Chemistry. Photosynthesis can be an ideal example to illustrate a green process explaining all the features such as selection of raw materials, solvent, catalyst, energy, etc. for an environment-friendly reaction. From the same reaction, all the principles of Green Chemistry can be derived in a simpler way without the need of memorizing these in a set language. In this article, a few examples of green procedures for the synthesis of useful molecules have been illustrated in light of the knowledge of photosynthesis. The visible-light mediated reactions, organic reactions in water, and solvent-free organic reactions are discussed here for a practical illustration of Green synthesis.
Recent advances in the synthesis of bioactive five- and six-membered heterocycles catalyzed by heterogeneous metal catalysts
Green Synthetic Approaches for Biologically Relevant Heterocycles, 2021
Abstract The use of heterogeneous metal catalysts has received much interest for its primary adva... more Abstract The use of heterogeneous metal catalysts has received much interest for its primary advantages of ease of operation, easy recovery, and recyclability of catalysts. These features are of much significance in the context of green synthesis and applications in industry. This chapter highlights the recent progress in the synthesis of various five- and six-membered N-, O-, S-containing heterocycles utilizing a variety of heterogeneous-supported metal catalysts. These include pyrroles, pyrrolidines, indolizines, imidazoles, benzimidazoles, triazoles, pyridines and dihydropyridines, pyridinones, pyrimidines, pyrimidinones, benzofurans, furocoumarins, pyrans, chromenes, and a few fused heterocycles. The scopes and limitations of the procedures have been reported. The possible reaction pathways of several reactions are discussed for better understanding.
ChemistrySelect, 2018
An efficient C(sp2)-N cross coupling of cyclic and acyclic amides with styrenyl/aryl/heteroaryl h... more An efficient C(sp2)-N cross coupling of cyclic and acyclic amides with styrenyl/aryl/heteroaryl halides catalyzed by cobalt acetylacetonate in combination with copper(I) iodide, has been achieved. A library of diversely substituted cyclic and acyclic enamides have been obtained in high yields by this procedure. The reaction is stereoselective producing (E)-enamides from trans-styrenyl halides and (Z)-products from cis-halides. This procedure has been successfully employed for the coupling of other N-heterocycles such as pyrazole, imidazole and triazole with aryl/styrenyl/heteroaryl halides to produce the corresponding N-coupled products. A probable mechanism has been suggested.
ChemistrySelect, 2020
A convenient method has been developed for the synthesis of biarenyl chalcogenides through the in... more A convenient method has been developed for the synthesis of biarenyl chalcogenides through the interaction of bicyclic arenes and diaryl dichalcogenides on the surface of basic alumina under ball milling without any metal catalyst or solvent. This methodology shows wide substrate scope and is of high potential in organic synthesis due to its green aspects of ease of operation, shorter reaction time, ambient conditions and high yields.
Copper catalyzed cyanation through CC bond cleavage of gem-aryl dibromide followed by second cyanation of iodoarene by a released CN unit
Organic Chemistry Frontiers, 2018
A new approach for the synthesis of aryl cyanides through CC cleavage of styrenyl gem-dibromide ... more A new approach for the synthesis of aryl cyanides through CC cleavage of styrenyl gem-dibromide has been achieved.
The Journal of Organic Chemistry, 2018
An efficient method for the C(sp 2)-amidation of 8-aminoquinoline benzamide by acyl azide in the ... more An efficient method for the C(sp 2)-amidation of 8-aminoquinoline benzamide by acyl azide in the presence of copper acetate has been achieved via C-H activation. Interestingly, the loading of copper acetate has strong influence on the outcome of the reaction. The use of one equivalent of copper acetate produces the corresponding aroyl amide, whereas, the use of two equivalents led to acetyl amide. A series of substituted benzoyl and acetyl amides have been obtained. Cu(OAc)2.H2O K2CO3 CH3CN 2 Cu(OAc)2.H2O K2CO3 DCE-3 Cu(OAc)2.H2O K2CO3 DMF 17 4 Cu(OAc)2.H2O K2CO3 DMSO 71 5 Cu(OAc)2.H2O K2CO3 Toluene-6 Cu(OAc)2.H2O K2CO3 MeOH-7 Cu(OAc)2.H2O K2CO3 H2O 19 8 Cu(OAc)2.H2O Cs2CO3 DMSO-9 Cu(OAc)2.H2O NaOAC DMSO 20 10 Cu(OAc)2.H2O Na2CO3 DMSO 29 11 Cu(OAc)2.H2O Et3N DMSO trace 12 Cu(OAc)2.H2O K3PO4 DMSO 17 20 c Cu(OAc)2.H2O K2CO3 DMSO 15 21 Co(OAc)2 K2CO3 DMSO-22 Ni(OAc)2 K2CO3 DMSO trace 23 d Cu(OAc)2.H2O K2CO3 DMSO 61 24 e Cu(OAc)2.H2O K2CO3 DMSO 69
Visible Light Photocatalyzed Carbon-Heteroatom Bond Formation and Synthesis of Related Compounds
Current Green Chemistry, 2017
New Journal of Chemistry, 2016
An efficient C(sp2)–P cross coupling has been achieved using a Co/Cu catalytic system for access ... more An efficient C(sp2)–P cross coupling has been achieved using a Co/Cu catalytic system for access to vinyl and aryl phosphonates.
Arkivoc, 2019
The inert C-H bond functionalization via bond activation in the presence of transition metals usi... more The inert C-H bond functionalization via bond activation in the presence of transition metals using ball milling is reviewed. The use of several transition metals, such as Pd, Rh, Ru, Co, and Ir are covered in this review for a variety of important functionalizations, including halogenation, amidation, alkynylation, and dehydrogenative coupling, among others. These reactions are performed under mild conditions, usually without any solvent, and in relatively short reaction times.
Organic letters, Feb 16, 2018
A cobalt-catalyzed selective remote C-4 alkylation of 8-aminoquinoline amides via C-H activation ... more A cobalt-catalyzed selective remote C-4 alkylation of 8-aminoquinoline amides via C-H activation under irradiation with a CFL lamp in the presence of eosin Y at room temperature has been achieved. A series of pharmaceutically important C-4 quinoline amide-substituted ether derivatives has been obtained by this procedure. The C-4 functionalization of quinoline amides with inert ether is of much significance and was not reported earlier.