Article
Chemistry, Organic
Kento Asai, Masahiro Miura, Koji Hirano
Summary: A palladium-catalyzed cross-coupling reaction between diarylmethanol derivatives and diborylmethane has been developed, delivering the corresponding homobenzylic boronates in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Nanxing Gao, Yanshun Li, Guorui Cao, Dawei Teng
Summary: The cross-electrophile coupling of aryl bromides and cyclic secondary alkyl bromides catalyzed by nickel/spiro-bidentate-pyox ligands with lithium chloride as the additive for Csp(2)-Csp(3) bond formation was reported. Various aryl-cyclic secondary alkyl Csp(2)-Csp(3) bond products were successfully synthesized under optimal reaction conditions.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Tanumay Roy, Krishanu Mondal, Arunava Sengupta, Parthasarathi Das
Summary: An efficient N-arylation reaction of hydantoins with substituted aryl/heteroaryl boronic acids has been developed using CuF2/MeOH as the catalyst under base and ligand-free conditions at room temperature and open air. The reaction is general and provides excellent yields of various N-arylated hydantoins with exclusive regioselectivity. The study also explores the selective N3-arylation of nucleosides and demonstrates the gram-scale synthesis of the drug Nilutamide. A mechanistic study reveals the importance of hydantoin and MeOH in the generation of catalytically active copper species, and the proposed reaction mechanism suggests the favorable N3-arylation of hydantoin in MeOH due to the formation of a square-planar Cu(II) complex with strong hydrogen-bond interactions. This research provides valuable insights into Cu(II)-catalyzed oxidative N-arylation reactions and has implications for the design and development of Cu-catalyzed coupling reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Maddali L. N. Rao, Sachchida Nand
Summary: The threefold cross-coupling of triarylbismuth reagents with 4-chloro-3-formylcoumarins using Pd-catalyzed conditions successfully provided the corresponding 4-aryl-3-formylcoumarins in a chemoselective manner with high yields. This method was applicable to electronically different triarylbismuth reagents and 4-chloro-3-formylcoumarins while preserving the 3-formyl group in the coumarin scaffold.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Matthew B. Minus, Sarah R. Moor, Fathima F. Pary, L. P. T. Nirmani, Malgorzata Chwatko, Brandon Okeke, Josh E. Singleton, Toby L. Nelson, Nathaniel A. Lynd, Eric Anslyn
Summary: The bimetallic methodology described in the study takes advantage of the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations under ambient conditions. The process is facile and can be performed by simple mixing in an open vessel. This method demonstrates its utility in polymer synthesis by successfully creating various polymers at ambient temperature and open to air.
Article
Chemistry, Organic
Shiyang Xu, Hong Guo, Yuhan Liu, Wenxu Chang, Jiyao Feng, Xiongkui He, Zhenhua Zhang
Summary: Due to the importance of polyfunctional amines, the formation of C-N bonds is crucial in synthetic organic chemistry. This study presents a neutral amination reaction utilizing azides as the nitrogen source and arylboronic acids with a rhodium(I) catalyst, leading to the synthesis of alkyl-aryl and aryl-aryl secondary amines. The utility of this method was demonstrated through the application to natural products and pharmaceutical derivatives, as well as gram-scale reactions. Mechanistic experiments and DFT calculations indicated the involvement of a metal-nitrene intermediate in the reaction.
Article
Chemistry, Physical
Jinhui Li, Ying Wang, Huilin Xie, Shangfeng Ren, Jin-Biao Liu, Nianhua Luo, Guanyinsheng Qiu
Summary: An efficient iron-catalyzed synthesis of N-aryl amides from N-methoxy amides and arylboronic acids is developed, in which FeCl3 is used as the sole catalyst for the cross-coupling reaction, resulting in moderate to excellent yields of N-aryl amides.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Organic
Wei Wei, Xiaodan Zhao
Summary: The carbon-carbon bond-forming cross-dehydrogenative coupling reaction using organoselenium catalysis involving a high-valent para-methoxyphenyl selenium species has been developed. This method enables the synthesis of alpha,alpha-disubstituted alpha-amino acid derivatives with excellent regioselectivities through vinyl or allylic C-H functionalization. The generality of this method has been demonstrated by the cross-coupling of an alkene with an oxindole and the direct functionalization of electron-rich arenes with azlactones.
Article
Chemistry, Organic
Dusty Cadwallader, Dmytro Shevchuk, Tristan R. Tiburcio, Christine M. Le
Summary: This study presents a method for the synthesis of alkynamides through the cross-coupling of carbamoyl fluorides and alkynylsilanes catalyzed by tetrabutylammonium fluoride (TBAF). It achieves C-F bond cleavage under mild conditions without the need for strongly nucleophilic reagents and/or catalysts, offering advantages over transition-metal-catalyzed approaches in terms of tolerance to aryl halide moieties and complementary chemoselectivity.
Article
Biochemistry & Molecular Biology
Huimin Wang, Shuqin Zhang, Minling Xu, Gang Zou
Summary: Researchers have developed a practical and efficient Suzuki coupling reaction of phenols using trans-NiCl(o-Tol)(PCy3)(2)/2PCy(3) as a catalyst and tosyl fluoride as an activator. The compatibility of the nickel catalyst with tosyl fluoride and its fluorosulfate exchange reaction with C-Ar-OH are crucial for the direct use of phenols. Water improves the one-pot reaction significantly, and a variety of electronically and sterically diverse biaryls can be obtained in good yields using 3-10 mol% of the nickel catalyst.
Review
Chemistry, Multidisciplinary
Michael G. J. Doyle, Rylan J. Lundgren
Summary: The Cu-catalyzed oxidative cross-coupling of N- and O-nucleophiles with aryl boronic acids (the Chan-Lam reaction) is a valuable method for preparing aniline and phenol derivatives, with high chemoselectivity and mild reaction conditions. In addition, we have developed the analogous carbon-carbon bond forming variant for the first time.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Felipe Verdugo, Ricardo Rodino, Martin Calvelo, Jose Luis Mascarenas, Fernando Lopez
Summary: The reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) can be directed towards tandem cycloisomerization/cross-coupling processes by using Pd-0 catalysts with phosphorus-based monodentate ligands. This allows for the synthesis of a wide variety of highly functionalized cyclic alcohols and amines through the formation of key pi-allyl oxapalladacyclic intermediates which are trapped with external nucleophilic partners.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Vincent M. Kassel, Christopher M. Hanneman, Connor P. Delaney, Scott E. Denmark
Summary: Reaction conditions have been developed for refractory heteroaryl-heteroaryl Suzuki-Miyaura cross-couplings using neopentyl heteroarylboronic esters, heteroaryl bromides and chlorides, and potassium trimethylsilanolate (TMSOK) under anhydrous conditions. The addition of trimethyl borate enhances reaction rates by several mechanisms, enabling cross-coupling of diverse reaction partners in good yields and short reaction times.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Jiajia Li, Junmin Chen, Hefeng Zhu, Mingzhong Cai
Summary: A new mesoporous SBA-15-anchored triphenylphosphine-gold(i) complex [SBA-15-Ph(3)PauNTf(2)] was synthesized and characterized. This catalyst allowed for the photosensitizer-free cross-coupling reaction of aryldiazonium tetrafluoroborates and alkynyltrimethylsilanes under blue LED irradiation, yielding diverse arylalkynes with good yields and high functional group tolerance. The catalyst could be easily recovered and reused multiple times without significant loss in activity.
NEW JOURNAL OF CHEMISTRY
(2023)
Letter
Chemistry, Organic
Kento Yasumoto, Noritaka Kunitomo, Taichi Kano
Summary: The Cu-catalyzed asymmetric conjugate addition of trialkenylboroxines to enone diesters is described. This operationally simple and scalable reaction proceeds at room temperature and tolerates a wide range of substrates. The practical utility of this method is demonstrated through the formal synthesis of (+)-methylenolactocin. Mechanistic studies reveal the synergistic action of two different catalytic species.
Review
Chemistry, Multidisciplinary
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
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
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
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
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
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
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
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
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
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
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)