Devesh Chandra | G.B.P.U.A.&T., PANTNAGAR, UTTARAKHAND, INDIA (original) (raw)

Papers by Devesh Chandra

Coordination Chemistry Reviews

European Journal of Organic Chemistry, Jul 12, 2023

An efficient Rh(III)‐catalyzed C−H alkenylation of N‐protected isoquinolone with maleimides is re... more An efficient Rh(III)‐catalyzed C−H alkenylation of N‐protected isoquinolone with maleimides is reported. The carbonyl group of isoquinolone acts as an inherent directing group. Various N‐substituents in the maleimide, including alkyl, aryl, and even H and −OH, were well tolerated under the developed reaction condition. This protocol showed broad substrate scope, good selectivity, and excellent yields. Hammett plot is also drawn to check the effect of substituents on the reaction progress.

Chemistry: A European Journal, Mar 11, 2020

Herein, the RhIII‐catalyzed selective monoarylation and diarylation (symmetrical and unsymmetrica... more Herein, the RhIII‐catalyzed selective monoarylation and diarylation (symmetrical and unsymmetrical) of 8‐methylquinolines with organoboron reagents are disclosed. The selective monoarylation of primary C(sp3)−H bonds is achieved by using 7‐substituted 8‐methylquinolines or by changing the quantity of the aryl boronic acids. The method is also applicable for the arylation of 2‐ethylpyridines, and the heteroarylation with thiophene‐2‐ylboronic acids. Symmetrical and unsymmetrical diarylation of 8‐methylquinolines have been carried out in one‐pot and sequential manner, respectively. Late‐stage monoarylation of oxime derivatives and gram‐scale synthesis of monoarylated products has also been carried out. A mechanistic study revealed that the current reaction is first order with respect to both reactants and a five‐membered rhodacycle intermediate may be involved in the catalytic cycle.

International Journal of Biological Macromolecules, Apr 1, 2023

Chemical Communications, 2022

Herein, the Rh(iii)-catalysed C(sp3)–H bond amidation of 8-methylquinolines using N-hydroxyphthal... more Herein, the Rh(iii)-catalysed C(sp3)–H bond amidation of 8-methylquinolines using N-hydroxyphthalimides as the amidation source is explored.

Chemical Communications, 2023

Chiral phosphoric acids can interact in different ways with the substrate to induce chirality int... more Chiral phosphoric acids can interact in different ways with the substrate to induce chirality into the system. This review summarizes the use of chiral phosphoric acids in the exciting field of enantioselective C–H activation.

European Journal of Organic Chemistry

An efficient Rh(III)‐catalyzed C−H alkenylation of N‐protected isoquinolone with maleimides is re... more An efficient Rh(III)‐catalyzed C−H alkenylation of N‐protected isoquinolone with maleimides is reported. The carbonyl group of isoquinolone acts as an inherent directing group. Various N‐substituents in the maleimide, including alkyl, aryl, and even H and −OH, were well tolerated under the developed reaction condition. This protocol showed broad substrate scope, good selectivity, and excellent yields. Hammett plot is also drawn to check the effect of substituents on the reaction progress.

Chemical Communications

Chiral phosphoric acids can interact in different ways with the substrate to induce chirality int... more Chiral phosphoric acids can interact in different ways with the substrate to induce chirality into the system. This review summarizes the use of chiral phosphoric acids in the exciting field of enantioselective C–H activation.

International Journal of Biological Macromolecules

Knowledge Updates 2022/2

The quinoline structure (also referred to as benzo[b]pyridine or 1-azanaphthalene) is the most ex... more The quinoline structure (also referred to as benzo[b]pyridine or 1-azanaphthalene) is the most explored heteroaromatic ring system, with compounds having this unit exhibiting pharmacological activities and featuring in several marketed drugs. Therefore, in this contibution, an update to the previous Science of Synthesis chapter on quinolines has been compiled, covering the literature reported between 2005 and 2020. Diverse routes to access the quinoline core, as well methods for the preparation of functionalized quinolines, have been collated, which originate from a wide array of starting materials. The strategies covered include condensations, annulations, metal-catalyzed approaches, oxidations, cyclizations, tandem reactions, and many more.

Chemical Communications

Herein, the Rh(iii)-catalysed C(sp3)–H bond amidation of 8-methylquinolines using N-hydroxyphthal... more Herein, the Rh(iii)-catalysed C(sp3)–H bond amidation of 8-methylquinolines using N-hydroxyphthalimides as the amidation source is explored.

Catalysis Reviews-science and Engineering, Aug 16, 2022

The Chemical Record, 2021

Direct functionalization of heterocycles using C−H activation widely relies on the precious metal... more Direct functionalization of heterocycles using C−H activation widely relies on the precious metal complexes. In past decade, the use of earth abundant and inexpensive transition metal to functionalize heterocycles has become an attractive alternate strategy. This concept is also interesting due to the unique reactivity pattern of these inexpensive metals. In this context we and other research groups have utilized the high‐valent cobalt complexes as an inexpensive and readily available catalyst for the functionalization of heterocycles. In this review, we intend to brief recent progress made in the area of high‐valent cobalt complexes catalyzed C−H functionalization of N‐containing heterocycles.

Journal of Essential Oil Bearing Plants, 2019

Zingiber chrysanthum Roscoe is a traditional medicinal plant species sparsely occurring in Kumaun... more Zingiber chrysanthum Roscoe is a traditional medicinal plant species sparsely occurring in Kumaun Lesser Himalaya, Uttarakhand. Seeds of this species were collected from wild populations and essential oil was extracted. This essential oil was phytochemically analyzed by GC/MS and various biological activities viz: antioxidant, anti-inflammatory, antibacterial were also performed using standard protocols. More than 92 compounds were identified from essential oil of the seed. β-pinene (36.3 %) is identified as major product of the oil followed by α-pinene (9.3 %), limonene (5.4 %), γ-terpinene (5.0 %), (E)-caryophyllene (4.0 %), α-terpineol (3.6 %) and terpenin-4-ol (3.2 %) suggesting a greater efficacy of plant in flavor, decorative and non decorative cosmetic industry. The essential oil showed strong antioxidant activity in terms of DPPH (IC 50 =10.81±0.03 μL/ mL), metal chelating (IC 50 =16.84±0.46 μL/mL) and reducing power activity (RP 50 = 15.55±0.02 μL/mL). Antiinflammatory activity in terms of protein denaturation (IB 50 =16.76±0.00 μL/mL) and a moderate antibacterial activity was also reported against the bacterial strains E. coli and S. aureus by the Z. chrysanthum seed essential oil.

European Journal of Organic Chemistry, 2019

Herein rapid microwave assisted, (±) camphor-10-sulfonic acid (CSA) promoted Povarov type multico... more Herein rapid microwave assisted, (±) camphor-10-sulfonic acid (CSA) promoted Povarov type multicomponent synthesis of 4arylated quinolines from anilines, alkynes, and paraformaldehyde is described. This reaction proceeds through [4+2] cycloaddition of imine (formed in situ from aniline and paraformaldehyde) and alkynes in presence of CSA, without any metal catalyst. Mechanistic study revealed that CSA inhibit the synthesis of Troger's base and assist the cycloaddition of imine with alkyne by activating imine.

RSC Advances

High reducible distorted bimetallic sites with medium size in Ni5Co5-AC promoted the production o... more High reducible distorted bimetallic sites with medium size in Ni5Co5-AC promoted the production of cyclohexanol by hydrogenation of anisole and subsequent cleavage of C6H11O–CH3 bond.

Advanced Synthesis & Catalysis

Organic & Biomolecular Chemistry

This review summarizes the recent advancements in transition-metal (TM) catalyzed enantioselectiv... more This review summarizes the recent advancements in transition-metal (TM) catalyzed enantioselective C–H activation via kinetic resolution approach.

Coordination Chemistry Reviews

European Journal of Organic Chemistry, Jul 12, 2023

An efficient Rh(III)‐catalyzed C−H alkenylation of N‐protected isoquinolone with maleimides is re... more An efficient Rh(III)‐catalyzed C−H alkenylation of N‐protected isoquinolone with maleimides is reported. The carbonyl group of isoquinolone acts as an inherent directing group. Various N‐substituents in the maleimide, including alkyl, aryl, and even H and −OH, were well tolerated under the developed reaction condition. This protocol showed broad substrate scope, good selectivity, and excellent yields. Hammett plot is also drawn to check the effect of substituents on the reaction progress.

Chemistry: A European Journal, Mar 11, 2020

Herein, the RhIII‐catalyzed selective monoarylation and diarylation (symmetrical and unsymmetrica... more Herein, the RhIII‐catalyzed selective monoarylation and diarylation (symmetrical and unsymmetrical) of 8‐methylquinolines with organoboron reagents are disclosed. The selective monoarylation of primary C(sp3)−H bonds is achieved by using 7‐substituted 8‐methylquinolines or by changing the quantity of the aryl boronic acids. The method is also applicable for the arylation of 2‐ethylpyridines, and the heteroarylation with thiophene‐2‐ylboronic acids. Symmetrical and unsymmetrical diarylation of 8‐methylquinolines have been carried out in one‐pot and sequential manner, respectively. Late‐stage monoarylation of oxime derivatives and gram‐scale synthesis of monoarylated products has also been carried out. A mechanistic study revealed that the current reaction is first order with respect to both reactants and a five‐membered rhodacycle intermediate may be involved in the catalytic cycle.

International Journal of Biological Macromolecules, Apr 1, 2023

Chemical Communications, 2022

Herein, the Rh(iii)-catalysed C(sp3)–H bond amidation of 8-methylquinolines using N-hydroxyphthal... more Herein, the Rh(iii)-catalysed C(sp3)–H bond amidation of 8-methylquinolines using N-hydroxyphthalimides as the amidation source is explored.

Chemical Communications, 2023

Chiral phosphoric acids can interact in different ways with the substrate to induce chirality int... more Chiral phosphoric acids can interact in different ways with the substrate to induce chirality into the system. This review summarizes the use of chiral phosphoric acids in the exciting field of enantioselective C–H activation.

European Journal of Organic Chemistry

An efficient Rh(III)‐catalyzed C−H alkenylation of N‐protected isoquinolone with maleimides is re... more An efficient Rh(III)‐catalyzed C−H alkenylation of N‐protected isoquinolone with maleimides is reported. The carbonyl group of isoquinolone acts as an inherent directing group. Various N‐substituents in the maleimide, including alkyl, aryl, and even H and −OH, were well tolerated under the developed reaction condition. This protocol showed broad substrate scope, good selectivity, and excellent yields. Hammett plot is also drawn to check the effect of substituents on the reaction progress.

Chemical Communications

Chiral phosphoric acids can interact in different ways with the substrate to induce chirality int... more Chiral phosphoric acids can interact in different ways with the substrate to induce chirality into the system. This review summarizes the use of chiral phosphoric acids in the exciting field of enantioselective C–H activation.

International Journal of Biological Macromolecules

Knowledge Updates 2022/2

The quinoline structure (also referred to as benzo[b]pyridine or 1-azanaphthalene) is the most ex... more The quinoline structure (also referred to as benzo[b]pyridine or 1-azanaphthalene) is the most explored heteroaromatic ring system, with compounds having this unit exhibiting pharmacological activities and featuring in several marketed drugs. Therefore, in this contibution, an update to the previous Science of Synthesis chapter on quinolines has been compiled, covering the literature reported between 2005 and 2020. Diverse routes to access the quinoline core, as well methods for the preparation of functionalized quinolines, have been collated, which originate from a wide array of starting materials. The strategies covered include condensations, annulations, metal-catalyzed approaches, oxidations, cyclizations, tandem reactions, and many more.

Chemical Communications

Herein, the Rh(iii)-catalysed C(sp3)–H bond amidation of 8-methylquinolines using N-hydroxyphthal... more Herein, the Rh(iii)-catalysed C(sp3)–H bond amidation of 8-methylquinolines using N-hydroxyphthalimides as the amidation source is explored.

Catalysis Reviews-science and Engineering, Aug 16, 2022

The Chemical Record, 2021

Direct functionalization of heterocycles using C−H activation widely relies on the precious metal... more Direct functionalization of heterocycles using C−H activation widely relies on the precious metal complexes. In past decade, the use of earth abundant and inexpensive transition metal to functionalize heterocycles has become an attractive alternate strategy. This concept is also interesting due to the unique reactivity pattern of these inexpensive metals. In this context we and other research groups have utilized the high‐valent cobalt complexes as an inexpensive and readily available catalyst for the functionalization of heterocycles. In this review, we intend to brief recent progress made in the area of high‐valent cobalt complexes catalyzed C−H functionalization of N‐containing heterocycles.

Journal of Essential Oil Bearing Plants, 2019

Zingiber chrysanthum Roscoe is a traditional medicinal plant species sparsely occurring in Kumaun... more Zingiber chrysanthum Roscoe is a traditional medicinal plant species sparsely occurring in Kumaun Lesser Himalaya, Uttarakhand. Seeds of this species were collected from wild populations and essential oil was extracted. This essential oil was phytochemically analyzed by GC/MS and various biological activities viz: antioxidant, anti-inflammatory, antibacterial were also performed using standard protocols. More than 92 compounds were identified from essential oil of the seed. β-pinene (36.3 %) is identified as major product of the oil followed by α-pinene (9.3 %), limonene (5.4 %), γ-terpinene (5.0 %), (E)-caryophyllene (4.0 %), α-terpineol (3.6 %) and terpenin-4-ol (3.2 %) suggesting a greater efficacy of plant in flavor, decorative and non decorative cosmetic industry. The essential oil showed strong antioxidant activity in terms of DPPH (IC 50 =10.81±0.03 μL/ mL), metal chelating (IC 50 =16.84±0.46 μL/mL) and reducing power activity (RP 50 = 15.55±0.02 μL/mL). Antiinflammatory activity in terms of protein denaturation (IB 50 =16.76±0.00 μL/mL) and a moderate antibacterial activity was also reported against the bacterial strains E. coli and S. aureus by the Z. chrysanthum seed essential oil.

European Journal of Organic Chemistry, 2019

Herein rapid microwave assisted, (±) camphor-10-sulfonic acid (CSA) promoted Povarov type multico... more Herein rapid microwave assisted, (±) camphor-10-sulfonic acid (CSA) promoted Povarov type multicomponent synthesis of 4arylated quinolines from anilines, alkynes, and paraformaldehyde is described. This reaction proceeds through [4+2] cycloaddition of imine (formed in situ from aniline and paraformaldehyde) and alkynes in presence of CSA, without any metal catalyst. Mechanistic study revealed that CSA inhibit the synthesis of Troger's base and assist the cycloaddition of imine with alkyne by activating imine.

RSC Advances

High reducible distorted bimetallic sites with medium size in Ni5Co5-AC promoted the production o... more High reducible distorted bimetallic sites with medium size in Ni5Co5-AC promoted the production of cyclohexanol by hydrogenation of anisole and subsequent cleavage of C6H11O–CH3 bond.

Advanced Synthesis & Catalysis

Organic & Biomolecular Chemistry

This review summarizes the recent advancements in transition-metal (TM) catalyzed enantioselectiv... more This review summarizes the recent advancements in transition-metal (TM) catalyzed enantioselective C–H activation via kinetic resolution approach.