4.7 Article

An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: a new facet to classical DMSO oxidation

期刊

CHEMICAL COMMUNICATIONS
卷 51, 期 84, 页码 15438-15441

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc05713b

关键词

-

资金

  1. SERB, DST New Delhi [SR/FT/CS-92/2011]
  2. SEED Grant of IIT Mandi
  3. DST
  4. CSIR
  5. IIT Mandi

向作者/读者索取更多资源

A conceptually new dimethyl sulfoxide (DMSO) based oxidation process without the use of any activator has been demonstrated for the oxidation of active methylenes and benzhydrols. The developed protocol utilizes the electrophilic center of DMSO for oxidation, which was unexplored before. Mechanistic investigation has confirmed that the source of oxygen is DMSO.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Chemistry, Organic

Overcoming the Challenges toward Selective C(6)-H Functionalization of 2-Pyridone with Maleimide through Mn(I)-Catalyst: Easy Access to All-Carbon Quaternary Center

Smruti Ranjan Mohanty, Namrata Prusty, Shyam Kumar Banjare, Tanmayee Nanda, Ponneri C. Ravikumar

Summary: An earth-abundant and inexpensive Mn(I)-catalyzed alkylation of 2-pyridone with maleimide has been reported for the first time, which demonstrates an unexpected rearrangement in the presence of acetic acid and provides a unique class of compounds. This methodology shows good tolerance towards various functional groups, delivering the alkylated products in moderate to excellent yields.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Palladium-catalyzed selective C-C bond cleavage and stereoselective alkenylation between cyclopropanol and 1,3-diyne: one-step synthesis of diverse conjugated enynes

Bedadyuti Vedvyas Pati, Asit Ghosh, Komal Yadav, Shyam Kumar Banjare, Shalini Pandey, Upakarasamy Lourderaj, Ponneri C. Ravikumar

Summary: The stereoselective synthesis of 1,3-enynes from 1,3-diynes was achieved by palladium-catalyzed selective C-C bond cleavage of cyclopropanol. The protocol showed high stereoselectivity with diverse substrates. Mechanistic investigations and DFT calculations were carried out to validate the atomic-level mechanism and identify rate-controlling states in the catalytic cycle. Preliminary investigations ruled out the involvement of the radical pathway in this transformation.

CHEMICAL SCIENCE (2022)

Review Engineering, Environmental

Microplastics removal strategies: A step toward finding the solution

Neha Badola, Ashish Bahuguna, Yoel Sasson, Jaspal Singh Chauhan

Summary: Microplastics are a growing threat to the environment, especially in water ecosystems. Scientists are researching various methods to remove microplastics, but there are limitations to their efficiency and applicability in different environmental conditions. Additionally, implementing governmental policies and regulations against microplastics remains a challenging task. This review aims to provide an overview of effective microplastic removal methods, compare their mechanisms and limitations, and discuss global policies and regulations. The review also highlights research gaps and recent advancements in the field.

FRONTIERS OF ENVIRONMENTAL SCIENCE & ENGINEERING (2022)

Article Chemistry, Organic

Pyridone Directed Ru-Catalyzed Olefination ofsp2(C-H) Bond UsingMichael Acceptors: Creation of Drug Analogues

Smruti Ranjan Mohanty, Namrata Prusty, Tanmayee Nanda, Shyam Kumar Banjare, Ponneri C. Ravikumar

Summary: In this study, the ruthenium-catalyzed regioselective sp2(C-H) monoalkenylation of N-arylpyridones was demonstrated, where the pyridone served as a weakly coordinating directing group. Importantly, this methodology was effectively applied to the synthesis of various drug analogues, with high yields up to 93%. HRMS analysis also revealed the presence of a six-membered ruthenium complex.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Co(II)-Catalysed C-H/N-H Annulation of Cyclic Alkenes with Benzamides at Room Temperature: An Easy Access to the Core Skeleton of Hexahydrobenzo[c]phenanthridine-type Alkaloids

Gopal Krushna Das Adhikari, Bedadyuti Vedvyas Pati, Smruti Ranjan Mohanty, Namrata Prusty, Ponneri C. Ravikumar

Summary: A highly regio- and stereoselective synthesis of the core skeleton of hexahydrobenzo[c]phenanthridine-type alkaloids using Co(acac)(2) at room temperature is reported. The reaction shows compatibility for a wide range of substrates and provides good to excellent yield of products.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Rhodium-Catalyzed Selective C(sp2)-H Activation/Annulation of tert-Butyl Benzoyloxycarbamates with 1,3-Diynes: A One Step Access to Alkynylated Isocoumarins and Bis-Isocoumarins

Bedadyuti Vedvyas Pati, Shyam Kumar Banjare, Gopal Krushna Das Adhikari, Tanmayee Nanda, Ponneri C. Ravikumar

Summary: In this study, a Rh(III) catalyzed synthesis of alkynylated and bis-isocoumarin compounds from 1,3-dialkyne was reported. Exclusive one-pot formation of 3,3-bis-isocoumarin isomers was achieved, eliminating several other possibilities. This is the first example of transition metal catalyzed synthesis of alkynylated and bis-isocoumarin scaffolds, and the protocol is compatible with a wide range of functional groups.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Switching the Reactivity of the Nickel-Catalyzed Reaction of 2-Pyridones with Alkynes: Easy Access to Polyaryl/Polyalkyl Quinolinones

Namrata Prusty, Smruti Ranjan Mohanty, Shyam Kumar Banjare, Tanmayee Nanda, Ponneri C. Ravikumar

Summary: A Ni-catalyzed cascade reaction between 2-pyridone and alkynes has been achieved by tuning reaction conditions and incorporating a directing group. The use of sodium iodide as an additive plays a crucial role in the success of this transformation. The detection of a five-membered metallacycle intermediate through HRMS provides insights into the reaction mechanism.

ORGANIC LETTERS (2022)

Review Chemistry, Physical

Recent Advancement in Palladium-Catalyzed C-C Bond Activation of Strained Ring Systems: Three- and Four-Membered Carbocycles as Prominent C3/C4 Building Blocks

Tanmayee Nanda, Muhammed Fastheem, Astha Linda, Bedadyuti Vedvyas Pati, Shyam Kumar Banjare, Pragati Biswal, Ponneri C. Ravikumar

Summary: In recent years, the strong C-C bond activation catalyzed by transition metals has gained significant attention in the field of synthetic chemistry. This protocol allows for the simultaneous and direct functionalization of two different M-C bonds. Among various strategies for C-C bond activation, strain-driven C-C bond activation has enabled otherwise challenging transformations. Palladium catalysts have been extensively explored and utilized due to their robust reactivity and selectivity. In this article, we briefly discuss the palladium-catalyzed C-C bond activation of three- and four-membered cycloalkane derivatives.

ACS CATALYSIS (2022)

Article Chemistry, Multidisciplinary

N-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed stereoselective trans-propenylation of aryl C(sp2)-H bond

Pragati Biswal, Tanmayee Nanda, Shyam Kumar Banjare, Smruti Ranjan Mohanty, Ranjit Mishra, Ponneri C. Ravikumar

Summary: This article reports a novel reaction method for the highly stereoselective C(sp(2))-H propenylation using N-allyl benzimidazole as a catalyst. Detailed mechanistic studies were conducted to understand the reaction mechanism.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Applied

Uncovering the Reactivity of Cobalt-Catalyst Towards Regioselective Hydroarylation of 1,6-Diyne via Weak-Chelation Assisted C-H Bond Activation

Shyam Kumar Banjare, Saista Afreen, Pranav Shridhar Mahulkar, Annapurna Saxena, Ponneri C. Ravikumar

Summary: Here, we report the reactivity of cobalt(III)-catalyst towards hydroarylative functionalization of 1,6-diyne, and unveil the reaction mechanism and the involvement of an ionic pathway.

ADVANCED SYNTHESIS & CATALYSIS (2023)

Article Chemistry, Organic

Rhodium-Catalyzed Synthesis of 2-Methylindoles via C-N Bond Cleavage of N-Allylbenzimidazole

Pragati Biswal, Tanmayee Nanda, Namrata Prusty, Smruti Ranjan Mohanty, Ponneri C. Ravikumar

Summary: A rhodium-catalyzed oxidative C-H/N-H dehydrogenative[3 + 2] annulation strategy has been developed for the synthesis of 2-methylindole scaffolds by reacting anilines and N-allylbenzimidazole. This transformation involves the cleavage of the thermodynamically stable C-N bond of allylamine and proceeds through a cascade of C(sp(2))-H alkylation followed by intramolecular cyclization. Detailed mechanistic studies have been performed to identify a key intermediate.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Carboamination and olefination: ortho C-H functionalization of phenoxyacetamide

Tanmayee Nanda, Shubham Kumar Dhal, Gopal Krushna Das Adhikari, Namrata Prusty, Ponneri C. Ravikumar

Summary: We have demonstrated a rhodium-catalyzed carboamination of olefin with the double bond intact. For the first time, deacylative carboamination of the maleimide has been achieved using phenoxyacetamide as the aminating source. We have also disclosed a C-H olefination protocol where the maleimide group is successfully installed in the ortho-position of phenoxyacetamide, utilizing phenoxyacetamide as a traceless directing group with in situ release of acetamide. Base-assisted E2-elimination plays a key role in the success of the olefination reaction.

CHEMICAL COMMUNICATIONS (2023)

Review Chemistry, Organic

Transition metal-catalyzed C-H/C-C activation and coupling with 1,3-diyne

Bedadyuti Vedvyas Pati, Nitha Nahan Puthalath, Shyam Kumar Banjare, Tanmayee Nanda, Ponneri C. C. Ravikumar

Summary: This review provides an overview of recent developments in transition metal-catalyzed C-H/C-C bond activation and coupling with 1,3-diynes for assembling alkynylated heterocycles, bis-heterocycles, and 1,3-enynes. The use of 1,3-diynes has received significant attention due to its ability to easily form bis-heterocycles. The strategy of C-H activation and subsequent reaction with 1,3-diynes has potential for larger-scale synthesis in the pharmaceutical industry.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Article Chemistry, Organic

N-Heterocyclic carbene catalyzed base assisted C-C bond cleavage of cyclopropenones: an approach towards diastereoselective synthesis of azetidinones and benzoxazepines

Tanmayee Nanda, Asish Dharmendra Shukla, Shubham Kumar Dhal, Muhammed Fastheem, Ponneri C. Ravikumar

Summary: In this study, biologically active scaffolds, azetidinones or benzoxazepines, were synthesized through a series of reactions catalyzed by N-heterocyclic carbene. The key intermediate acylazolium species in this reaction is generated through C-C bond cleavage of cyclopropenone, which is different from previous N-heterocyclic carbene catalysis. Two different bio-active skeletons, beta-lactam and benzoxazepine, were successfully synthesized using N-heterocyclic carbene as the catalyst.

ORGANIC CHEMISTRY FRONTIERS (2023)

Article Chemistry, Multidisciplinary

Diverse reactivity of alkynes in C-H activation reactions

Shyam Kumar Banjare, Pranav Shridhar Mahulkar, Tanmayee Nanda, Bedadyuti Vedvyas Pati, Lamphiza O. Najiar, Ponneri C. Ravikumar

Summary: Alkynes play a crucial role as coupling partners in transition metal-catalysed reactions. Their ability to effectively coordinate with metal d-orbitals makes them highly versatile for the synthesis of valuable organic molecules. Despite extensive research, there is still a lot more to explore in terms of the reactivity of alkynes and their potential applications.

CHEMICAL COMMUNICATIONS (2022)

Review Chemistry, Multidisciplinary

Trap suppression in ordered organic photovoltaic heterojunctions

Dan He, Yawen Li, Fuwen Zhao, Yuze Lin

Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.

CHEMICAL COMMUNICATIONS (2024)

Review Chemistry, Multidisciplinary

Controversial mechanism of simultaneous photocatalysis and Fenton-based processes: additional effect or synergy?

Olivier Monfort, Arshitha Madhusudhan, Martin Motola

Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Polymerization of monomer aggregates for tailoring and patterning water wettability

Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna

Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Pd/Brønsted acid catalysed intramolecular N-allylation of indoles and pyrroles with alkynes for the synthesis of N-fused heterocycles

Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi

Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides

Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang

Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Modified minimal-size fragments of heparan sulfate as inhibitors of endosulfatase-2 (Sulf-2)

Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell

Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Reductive cyclodimerization of chalcones: exploring the self-adaptability of galvanostatic electrosynthesis

Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini

Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed oxidative [4+2] annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols

Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar

Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

PbTeB4O9: a lead tellurium borate with unprecedented fundamental building block [B4O10] and large birefringence

Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan

Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Wafer-scale synthesis of two-dimensional ultrathin films

Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal

Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Precise design of copolymer-conjugated nanocatalysts for active electron transfer

Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi

Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.

CHEMICAL COMMUNICATIONS (2024)