Review
Chemistry, Organic
Cheng Gong, Jian Tang, Fei Xu, Pengjie Li, Zetian Wang, Yumin Zhang, Guoxian Yu, Liang Wang
Summary: This article summarizes the recent advances in transition-metal-catalyzed C-H activation of pyridone/isoquinolone derivatives, focusing on catalytic systems, reaction mechanisms, substrate scopes, and synthetic applications.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Maria Valle, Marta Ximenis, Xabier Lopez de Pariza, Julian M. W. Chan, Haritz Sardon
Summary: Organocatalysis has become an effective complement to metal- or enzyme-based catalysis in polymer chemistry, with applications in polymerization, polymer functionalization, and depolymerization. Organocatalysts have advantages in ease of removal and sustainability compared to transition-metal-based catalysts, driving development in specialty applications such as medical devices, drug delivery, and optoelectronics. The use of organocatalysis and other organomediated reactions in polymer chemistry is rapidly expanding, especially in areas like controlled radical polymerization, additive manufacturing, and chemical recycling.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Qian-Yu Li, Yuhang He, Yu-Mei Lin, Lei Gong
Summary: Photo-induced methylation is a valuable method for introducing methyl groups into organic molecules, especially in pharmaceutical chemistry. This article provides a comprehensive review of photochemical strategies for direct and selective methylation of different types of C-H bonds. These advancements are expected to drive progress in organic synthesis, photocatalysis, and pharmaceutical development.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Seo Jin Yun, Jisu Kim, Eunsu Kang, Hoimin Jung, Hyun Tae Kim, Minkyu Kim, Jung Min Joo
Summary: The development of ligands and their roles in the catalytic cycle are crucial for achieving high efficiency and selectivity in nondirected transition-metal-catalyzed C-H functionalization. In this study, pyrazolopyridone (PzPyOH) ligands were developed for Pd-catalyzed perdeuteration and meta-selective alkenylation. The ligands facilitated C-H cleavage and enabled perdeuteration due to the incorporation of the 2-pyridone moiety, and the ligand properties allowed for selective functionalization of meta-positions in alkenylation.
Article
Chemistry, Physical
Seo Jin Yun, Jisu Kim, Eunsu Kang, Hoimin Jung, Hyun Tae Kim, Minkyu Kim, Jung Min Joo
Summary: The development of ligands and their role in catalytic cycles are essential for achieving high efficiency and selectivity in non-directed transition metal catalyzed C-H functionalization. In this study, a series of pyrazolopyridone (PzPyOH) ligands were designed for Pd-catalyzed perdeuteration and meta-selective alkenylation of arenes. The ligands incorporate a 2-pyridone moiety as an internal base, allowing for reversible C-H activation and enabling perdeuteration. The ligands also exhibit flexibility in binding to Pd, facilitating coordination with alkene coupling partners during alkenylation.
Article
Chemistry, Applied
Jiao-Zhe Li, Lan Mei, Xue-Er Cai, Can-Can Zhang, Ting-Ting Cao, Xun-Jie Huang, Yi-Lin Liu, Wen-Ting Wei
Summary: In this study, a transition-metal-free radical cyclization of 2-arylbenzoimidazoles with unactivated alkanes in aqueous media is presented. By using di-tert-butyl peroxide (DTBP) to promote the C(sp(3))-H bond functionalization, various benzimidazo[2,1-a]isoquinolin-6(5H)-ones can be assembled. This strategy not only tolerates a wide range of alkanes and toluene derivatives, but also provides an approach for the functionalization of unactivated C(sp(3))-H bonds in aqueous media under transition-metal-free systems.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Physical
Prabhat Kumar Baroliya, Jaishri Chopra, Tanay Pal, Siddhartha Maiti, Shaeel Ahmed Al-Thabaiti, Mohamed Mokhtar, Debabrata Maiti
Summary: Supported metal nanoparticles have become an essential research area in catalysed chemical transformations, providing sustainable processes and efficient tuning of reactivity and recyclability. Various support materials have been investigated for their benefits in C-H functionalization, aiming to design efficient catalytic systems for future research.
Article
Chemistry, Organic
Hu Xiaojing, Guo Feixiang, Zhu Runqing, Zhou Bingqi, Zhang Tao, Fang Lizhen
Summary: p-Alkoxy phenol (p-AOPs) compounds were obtained by one-step selective hydroxylation of alkoxyl-aryl ethers with the transition metal ruthenium(II) as catalyst and [bis(trifluoroacetoxy)iodo]benzene (PIFA) as oxidant. These p-AOPs could be easily converted to quinone monoacetals (QMAs) after dearomatization. Condensation of the QMAs with ss-naphthols provided polycyclic benzofurans which have a wide application prospect. The protocol established in this paper offered a facile and reliable way for the synthesis of these important compounds.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Silvia Cattani, Gianpiero Cera
Summary: Iron-catalyzed C-H activation is an economical and efficient synthetic method with the advantages of low cost and low toxicity. This review presents the most recent examples of iron-catalyzed C-H functionalizations, focusing on modern synthetic strategies and mechanistic aspects. Iron-catalyzed C-H activation has great potential for sustainable development in organic chemistry.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Karunanidhi Murali, Luana A. Machado, Renato L. Carvalho, Leandro F. Pedrosa, Rishav Mukherjee, Eufranio N. Da Silva Junior, Debabrata Maiti
Summary: C-H functionalization has made significant advancements in synthetic organic chemistry, offering promising prospects in drug development and molecular architecture. The employment of novel metal catalysts and metal-free organic ligands has enabled selective activation of C-H bonds, overcoming previous challenges faced by chemists.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Youhao Wei, Zheng Wang, Kaifeng Wang, Jiang-Kai Qiu, Zhaoshan Wang, Haotian Li, Xiu Duan, Kai Guo, Xiaoguang Bao, Xinxin Wu
Summary: This study reports a copper-catalyzed allenic C(sp(2))-H cyanation with exceptional site-selectivity, addressing the challenge in synthetic chemistry of functionalizing allenic C(sp(2))-H bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Sumit Ghosh, Pranjal Pyne, Anogh Ghosh, Alakananda Hajra
Summary: This review summarizes the recent findings and developments in the ortho C-H functionalization of 2-aryl-2H-indazazoles, highlighting its significance in synthetic organic chemistry.
Review
Chemistry, Multidisciplinary
Mikel Oiarbide, Claudio Palomo
Summary: The catalyst-controlled functionalization of unmodified carbonyl compounds is an important operation in organic synthesis, especially when high levels of site- and stereo-selectivity can be achieved. Recent contributions in this field have shown that some subsets of enolizable substrates can now be functionalized through various types of activation mechanisms.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Organic
Arpana Tyagi, Naveen Yadav, Jabir Khan, Sanjay Singh, Chinmoy Kumar Hazra
Summary: Silicon-containing molecules have widespread applications in various research areas, and the transition-metal-free C-H silylation is an essential process for fabricating carbon-silicon bonds. This review focuses on recent developments in the field of silicon chemistry, particularly innovative transition-metal-free catalytic silylation using different strategies.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Alessia Mori, Sebastien Curpanen, Cristofer Pezzetta, Alejandro Perez-Luna, Giovanni Poli, Julie Oble
Summary: Furfural and related compounds, as building blocks of industrial interest, have gained attention as green alternatives to petroleum-derived compounds. This minireview summarizes the methods of direct C-H functionalization of furfurals without modifying the redox state of the aldehyde function, focusing on transition metal catalyzed functionalization of the heteroaromatic nucleus and C-H transformations of the aldehyde function.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Bidhan Ghosh, Aniruddha Biswas, Soumen Chakraborty, Rajarshi Samanta
CHEMISTRY-AN ASIAN JOURNAL
(2018)
Article
Chemistry, Organic
Saurabh Maity, Debapratim Das, Souradip Sarkar, Rajarshi Samanta
Article
Chemistry, Multidisciplinary
Aniruddha Biswas, Souradip Sarkar, Rajarshi Samanta
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Debapratim Das, Gopal Sahoo, Aniruddha Biswas, Rajarshi Samanta
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Satabdi Bera, Aniruddha Biswas, Rajarshi Samanta
Summary: Researchers focus on developing methods for synthesizing nitrogen-containing heterocycles, with a prominent strategy being regioselective C-H bond functionalizations through migratory insertion of metal-carbenes and nitrenes. This method can be used to construct various functionalized nitrogen heterocycles.
Article
Chemistry, Organic
Aniruddha Biswas, Subarna Pan, Rajarshi Samanta
Summary: An efficient and straightforward method has been developed to synthesize heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. This method offers a simple way to produce QUINOX and related compounds with high site selectivity, and the synthesized naphthols can be transformed into privileged ligands. Suitable resolution methods can directly provide axially chiral heterobiaryls.
Article
Chemistry, Organic
Satabdi Bera, Aniruddha Biswas, Juthi Pal, Lisa Roy, Supriya Mondal, Rajarshi Samanta
Summary: A Pd(II)-catalyzed oxidative naphthylation of unmasked 2-pyridone derivatives using a twofold internal alkyne as coupling partner is described. The reaction involves N-H/C-H activation and leads to polyarylated N-naphthyl 2-pyridones. Mechanistic studies suggest a plausible mechanism based on N-H/C-H activation. The photophysical properties of the N-naphthyl 2-pyridone derivatives are explored and show promising results.
Article
Multidisciplinary Sciences
Andreas M. M. Arnold, Philipp Dullinger, Aniruddha Biswas, Christian Jandl, Dominik Horinek, Tanja Gulder
Summary: The authors report the synthesis of (poly)cyclic carbon frameworks using in-situ formed fluorinated-alcohol-amine supramolecular clusters that mimic terpene cyclases. Terpene cyclases are highly efficient and selective catalysts in natural product synthesis. The supramolecular clusters act as artificial cyclases, triggering enzyme-like reactivity and selectivity by controlling substrate conformation in solution.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Julia Binder, Aniruddha Biswas, Tanja Gulder
Summary: In this study, a novel chlorination-induced polyene cyclization method is proposed, utilizing HFIP-chloroiodane networks to mimic terpene cyclases. Various different alkenes were converted with high selectivities (up to d.r. > 95:5). The cyclization platform was also successfully extended to structurally challenging terpenes and terpenoid carbon frameworks.
Article
Chemistry, Organic
Satabdi Bera, Aniruddha Biswas, Juthi Pal, Lisa Roy, Supriya Mondal, Rajarshi Samanta
Summary: In this paper, a Pd(II)-catalyzed oxidative naphthylation of unmasked 2-pyridone derivatives using a twofold internal alkyne as a coupling partner is described. The reaction proceeds through N-H/C-H activation to provide polyarylated N-naphthyl 2-pyridones. Mechanistic studies and DFT calculations suggest a plausible mechanism based on N-H/C-H activation. The photophysical properties of the N-naphthyl 2-pyridone derivatives were also studied.
Article
Chemistry, Multidisciplinary
Souradip Sarkar, Aniruddha Biswas, Sarbojit Das, Bortika Sanyal, Rajkumar Sahoo, Rajarshi Samanta
Summary: A rhodium(III)-catalyzed C4-selective cyanation of indole using N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as a coupling partner is described. The protocol showed a broad scope and achieved site selectivity by utilizing a weakly coordinating tert-amide group. The photophysical properties of the C4-cyanated indole frameworks were studied.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Souradip Sarkar, Aniruddha Biswas, Sarbojit Das, Bortika Sanyal, Rajkumar Sahoo, Rajarshi Samanta
Summary: This study describes a rhodium(III)-catalyzed indole C4-selective cyanation using the bench-stable and user-friendly electrophilic cyanation agent N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as a coupling partner. The selective site was achieved by utilizing a suitable weakly coordinating tert-amide group. The protocol developed in this study has a wide scope and [Cp*Rh(MeCN)(3)][SbF6](2) was identified as an effective Rh(III) catalyst. The photophysical properties of the C4-cyanated indole frameworks were also investigated.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Aniruddha Biswas, Satabdi Bera, Puja Poddar, Dibakar Dhara, Rajarshi Samanta
CHEMICAL COMMUNICATIONS
(2020)