Article
Chemistry, Multidisciplinary
Xiaolei Huang, Shenghan Teng, Yonggui Robin Chi, Wenqiang Xu, Maoping Pu, Yun-Dong Wu, Jianrong Steve Zhou
Summary: The nickel-catalyzed intermolecular Heck reaction of cycloalkenes with aryl triflates, mesylates, and tosylates shows excellent enantiomeric ratios. Additionally, the asymmetric reductive Heck reaction is also applicable to a 2-cyclopentenone ketal, equivalent to conjugate arylation of the enone itself.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Su Chen, Luc Van Meervelt, Erik V. Van der Eycken, Upendra K. Sharma
Summary: A mild visible-light-driven palladium-catalyzed radical tandem dearomatization reaction of indoles with unactivated alkenes is described. This reaction exhibited moderate to good yields and good to excellent diastereoselectivities. Under visible-light irradiation, a photo-excited state of the palladium complex was formed, which enabled the transfer of a single electron to N-(2-bromobenzoyl)indoles, leading to a hybrid palladium radical chemistry. This approach provides efficient and atom-economical access to diverse 2,3-disubstituted indoline derivatives.
Article
Chemistry, Multidisciplinary
Sumon Sarkar, Soumen Ghosh, Daria Kurandina, Yusuf Noffel, Vladimir Gevorgyan
Summary: Photoinduced enhancement of hydricity of palladium hydride species enables unprecedented hydride addition-like (hydridic) hydropalladation of electron-deficient alkenes, which allows for chemoselective head-to-tail cross-hydroalkenylation of electron-deficient and electron-rich alkenes. This mild and general protocol works with a wide range of densely functionalized and complex alkenes. Notably, this approach also allows for highly challenging cross-dimerization of electronically diverse vinyl arenes and heteroarenes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Yao Zhao, Shuangqiang Wang, Huihui Shao, Xuyong Tan, Rizhi Chen, Teck-Peng Loh, Jianrong Steve Zhou, Xiaojin Wu
Summary: Pd-catalyzed double Heck reaction enables regioselective 1,1-diarylation of unactivated aliphatic alkenes. The trans addition of the second aryl rings to aliphatic chains in the main olefinic isomers suggests a mechanism involving two consecutive Heck arylations at the terminal carbons.
Article
Chemistry, Organic
Tomoyuki Sekino, Shunta Sato, Tatsuhiko Yoshino, Masahiro Kojima, Shigeki Matsunaga
Summary: This study reports the deaminative allylation of Katritzky salts using cobalt/organophotoredox dual catalysis. The reaction enables regioselective allylation and overcomes the substrate limitations of existing protocols.
Article
Chemistry, Organic
Fuyang Yue, Jianyang Dong, Yuxiu Liu, Qingmin Wang
Summary: Here we describe a mild and general protocol for the alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones under visible light. The method allows for efficient functionalization of sulfones with a wide range of alkyl groups and can be scaled to gram levels. Its excellent tolerance to functional groups and mild conditions make it suitable for late-stage functionalization of natural products and drug molecules.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Ying Ding, Jinguo Long, Xianjie Fang
Summary: A nickel-catalyzed hydrocyanation of aliphatic allenes with excellent regioselectivity has been developed. This protocol features mild reaction conditions and good functional group tolerance, providing an efficient catalytic pathway to access various allylic nitriles containing quaternary carbon centers in a one-step fashion. Additionally, preliminary attempts were made to investigate an asymmetric version of this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Maxwell B. Haughey, Kirsten E. Christensen, Darren L. Poole, Timothy J. Donohoe
Summary: The successful synthesis of the complex taiwanschirin fused [8,6,5] core, representing challenging and biologically active targets, was achieved through a novel alkynylation reaction and intramolecular Heck reaction method.
Article
Chemistry, Organic
Fusheng Bie, Chengwei Liu, Michal Szostak, Xuejing Liu
Summary: A robust palladium-catalyzed decarbonylative alkynylation of aryl anhydrides is reported. The catalytic system of Pd(OAc)(2)/XantPhos and DMAP as a nucleophilic additive has been identified as effective promoters for decarbonylative Sonogashira alkynylation. The present process expands this reactivity to readily available aryl anhydrides as electrophilic reagents for decarbonylative alkynylation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Najmeh Nowrouzi, Mohammad Abbasi, Elham Shaikhi Shahidzadeh
Summary: In this study, cyanodithioformate salt was utilized as a sulfur source to react with aryl halides, resulting in the formation of diaryl disulfide. The diaryl disulfide then reacted with styrenes/alpha-methylstyrene, leading to the synthesis of beta-Hydroxy sulfides with high regioselectivity in good to excellent yields.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lei Xu, Shengqing Zhu, Liping Huo, Fan Chen, Wei Yu, Lingling Chu
Summary: This study reports a regioselective, intermolecular 1,2-addition of aryl bromides to alkynes enabled by the photocatalytic generation of bromine radicals via photoredox and nickel catalysis. The mild and redox-neutral protocol tolerates a wide range of (hetero)aryl bromides as well as alkynes, diynes, and enynes, generating diverse alkenyl bromides with exclusive regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Senjie Ma, Haoyu Fan, Craig S. Day, Yumeng Xi, John F. Hartwig
Summary: Remote hydrofunctionalizations of alkenes enable the incorporation of functional groups distal to carbon-carbon double bonds. This study presents a system for the remote hydroamination of disubstituted alkenes, selectively functionalizing the subterminal, unactivated, methylene position of an alkyl chain. The high regioselectivity and reaction rates are attributed to the electronic properties of the amine substituent and the ligand DIP-Ad-SEGPHOS, which was developed by considering the steric and electronic effects of ligand modules. The remote hydroamination is compatible with a diverse range of alkenes and aminopyridines, allowing for the regioconvergent synthesis of amines from isomeric mixtures of alkenes. The resulting products can be further modified through nucleophilic aromatic substitution reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Natalia A. Larionova, Jun Miyatake Ondozabal, Emily G. Smith, Xacobe C. Cambeiro
Summary: A photocatalytic method for alpha-selective hydroaminoalkylation of cinnamate esters has been developed, demonstrating regioselective addition of alpha-aminoalkyl radicals to unsaturated esters. The study expanded the scope to include styrenes with anti-Markovnikov selectivity, emphasizing the importance of the aromatic group at the beta-position. Simple scale-up under continuous flow conditions highlights the practicality of the method.
Article
Chemistry, Multidisciplinary
Lingxiang Lu, Yi Wang, Wendy Zhang, Wen Zhang, Kimberly A. See, Song Lin
Summary: The cross-electrophile dialkylation of alkenes allows for regioselective dialkylation of alkenes without the use of transition-metal catalysts, leading to the formation of two C-(sp(3))-C-(sp(3)) bonds. This method provides a modular and efficient approach to building structural complexity in organic synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Bowen Li, Bangke Luo, He Yang, Wenjun Tang
Summary: This study reports an efficient palladium-catalyzed Heck reaction for the synthesis of heterocycles with α-heteroaryl substitution. The method exhibits a broad substrate scope and excellent functional group compatibility. The use of a sterically bulky ligand containing an anthryl moiety is crucial for this transformation. Additionally, an asymmetric variant of the Heck reaction has been achieved, enabling the efficient asymmetric synthesis of (S)-nicotine and its analogues via a cationic palladium pathway.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Shenghan Teng, Zhiwei Jiao, Yonggui Robin Chi, Jianrong Steve Zhou
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Xiaolei Huang, Minh Hieu Nguyen, Maoping Pu, Luoqiang Zhang, Yonggui Robin Chi, Yun-Dong Wu, Jianrong Steve Zhou
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Xiaolei Huang, Shenghan Teng, Yonggui Robin Chi, Wenqiang Xu, Maoping Pu, Yun-Dong Wu, Jianrong Steve Zhou
Summary: The nickel-catalyzed intermolecular Heck reaction of cycloalkenes with aryl triflates, mesylates, and tosylates shows excellent enantiomeric ratios. Additionally, the asymmetric reductive Heck reaction is also applicable to a 2-cyclopentenone ketal, equivalent to conjugate arylation of the enone itself.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Shenghan Teng, Yonggui Robin Chi, Jianrong Steve Zhou
Summary: Asymmetric coupling efficiently occurs between propargylic acetates, cycloalkenes, and electron-rich heteroarenes, yielding 2,3-disubstituted tetrahydrofurans and pyrrolidines in trans configuration with excellent enantiomeric ratios. The reaction proceeds via Wacker-type attack of nucleophilic heteroarenes on alkenes activated by allenyl Pd-II species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Daoyong Zhu, Wenqiang Xu, Maoping Pu, Yun-Dong Wu, Yonggui Robin Chi, Jianrong Steve Zhou
Summary: This study revealed that palladium catalyzes a domino Heck arylation and alkylation of nonconjugated cyclodienes to produce trans isomers of disubstituted cyclohexenes with exceptionally high enantiomeric ratios. Through DFT calculations and experiments, it was demonstrated that the interaction between the two CF bonds of Josiphos and the sodium ion of malonates facilitates stereoselective allylic attack. This represents a new type of attractive noncovalent interactions discovered in organometallic catalysis.
Article
Chemistry, Multidisciplinary
Peng Yang, Yaxin Sun, Kaiyue Fu, Li Zhang, Guang Yang, Jieyu Yue, Yu Ma, Jianrong Steve Zhou, Bo Tang
Summary: A nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction was utilized to convert terminal alkynes to alpha-chiral carboxylic acids. The reaction showed high selectivity and efficiency in preparing biologically active compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Shenghan Teng, Jianrong Steve Zhou
Summary: This review summarizes the recent advances in transition metal-catalyzed asymmetric alkylation of heteroarenes using alkenes, covering literature from 2000 to late 2021. The reactions are classified into different categories based on the metal-mediated substrate activation, and the corresponding reaction mechanisms and catalyst design are discussed.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Organic
Huihui Shao, Yao Zhao, Shuangqiang Wang, Rizhi Chen, Jianrong Steve Zhou, Xiaojin Wu
Summary: This study developed a Pd-catalyzed chemo- and regiocontrollable 1,1-diarylation reaction that allows for the reaction of unactivated aliphatic alkenes with two aryl halides. In this process, the first aryl insertion reaction involves beta-H elimination, while the second aryl insertion reaction is terminated by C-H bond formation.
Article
Chemistry, Multidisciplinary
Jianrong Steve Zhou, Luoqiang Zhang, Xiuhua Wang, Maoping Pu, Caiyou Chen, Peng Yang, Yun-Dong Wu, Yonggui Robin Chi
Summary: Nickel catalysts with chiral pyrox ligands were used for enantioselective reductive arylation and heteroarylation of aldimines using (hetero)aryl halides and sulfonates. Crude aldimines generated from the condensation of aldehydes and azaaryl amines can also be used for catalytic arylation. The mechanism involves an elementary step of 1,4-addition of aryl nickel(I) complexes to N-azaaryl aldimines, as supported by density functional theory (DFT) calculations and experiments.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Yao Zhao, Shuangqiang Wang, Huihui Shao, Xuyong Tan, Rizhi Chen, Teck-Peng Loh, Jianrong Steve Zhou, Xiaojin Wu
Summary: Pd-catalyzed double Heck reaction enables regioselective 1,1-diarylation of unactivated aliphatic alkenes. The trans addition of the second aryl rings to aliphatic chains in the main olefinic isomers suggests a mechanism involving two consecutive Heck arylations at the terminal carbons.
Article
Chemistry, Multidisciplinary
Zhaoming Ma, Wenqiang Xu, Yun-Dong Wu, Jianrong Steve Zhou
Summary: Cobalt complexes of chiral pyrox ligands are used as catalysts for the enantioselective reductive coupling of nonconjugated iododienes with aryl iodides or alkenyl bromides. This reaction enables the stereoselective synthesis of 5-7-membered azacycles carrying quaternary stereocenters. Mechanistically, the selectivity of cross-electrophile coupling comes from the selective coupling of alkylcobalt(I) complexes generated after cyclization with aryl iodides.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Luoqiang Zhang, Dao-Yong Zhu, Jingyao Hu, Minjun Feng, Tze Chien Sum, Haoran Sun, Hajime Hirao, Yonggui Robin Chi, Jianrong Steve Zhou
Summary: In this study, direct alkylation of 5- and 6-membered heteroarenes, including azoles and azines, was achieved using alkanes, ethers, and carbamates under LED irradiation. Through the discovery of an organic photosensitizer, 9,10-dichloroanthracene, the overall efficiency of radical couplings was significantly increased via energy transfer of exciplexes, enabling successful oxidative couplings even with 1.5 equivalents of alkanes.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Zhaoming Ma, Lantian Sun, Jianrong Steve Zhou
Summary: The catalytic enantioselective domino alkenylation-heteroarylation reaction of nonconjugated iododienes shows excellent stereoselectivity and a wide range of substrate adaptability. The reaction enables the stereoselective synthesis of substituted azacycles carrying new quaternary stereocenters, such as piperidine, pyrrolidine azepine, and dihydropyrans. Mechanistically, the C-H bonds of heterocycles are activated by lithium alkoxides through reversible deprotonation, rather than conventional palladium(ii)-assisted metalation processes. Various types of heteroarenes can be used, including not only azoles (such as thiazoles, oxazoles, imidazoles, and oxadiazoles) but also nonazoles (thiophene, furan, and azine N-oxides).
Article
Chemistry, Multidisciplinary
Jianrong Steve Zhou, Siyu Guo, Xiaohu Zhao, Yonggui Robin Chi
Summary: Nickel complexes ligated by strongly donating diphosphines catalyze enantioselective hydrogenation for the preparation of acyclic and cyclic beta-amido esters, with a combination of acetic acid and indium powder providing protons and electrons to form nickel hydrido complexes under umpolung hydrogenation conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jianrong Steve Zhou, Xiaolei Huang, Shenghan Teng, Yonggui Robin Chi
Summary: Nickel-catalyzed Heck reaction of cycloalkenes produces unusual conjugated arylated isomers. The omission of bases allows nickel hydride species to perform in situ olefin isomerization of initial Heck adducts, enhancing the reactivity of aryl triflates, mesylates, tosylates, and pivalates.
CHEMICAL COMMUNICATIONS
(2021)
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)