Article
Chemistry, Organic
Bastian Jakob, Ichraf Slimani, Andreas Diehl, Naceur Hamdi, Georg Manolikakes
Summary: This study presents a palladium-catalyzed decarboxylative 1,2-addition of carboxylic acids to glyoxylic acid esters, providing access to the mandelic acid scaffold in good yields. The method utilizes readily available benzoic acids as a more sustainable alternative to preformed organometallic nucleophiles, showing promise for environmentally friendly organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Sangeth Jenthra, Totan Mondal, Gregor Kemper, Marcus Lantzius-Beninga, Markus Hoelscher, Walter Leitner
Summary: A highly chemo- and regioselective decarboxylative Heck-type coupling of carboxylic acids and terminal olefins was achieved using a catalytic system composed of Pd(OAc)(2) in the presence of phosphine-sulfonamido ligands. The bulky ligand L1 favored the formation of 1,1-disubstituted branched olefins with high selectivity, while the less bulky ligand L2 resulted in the formation of 1,2-disubstituted linear products in high yield. Detailed mechanistic investigation revealed that the aryl substituent at the sulfonamide group of ligand L1 favored 1,2-insertion, while the less bulky ligand L2 favored 2,1-insertion.
Article
Chemistry, Organic
Bo Jin, Ariamala Gopalsamy, Bo Peng, Li Sha, Sharon Tentarelli, Lakshmaiah Gingipalli
Summary: A photoredox-catalyzed decarboxylative addition of N-substituted acetic acids to aldehydes was developed for the synthesis of secondary alcohols. The successful implementation of this methodology relies on the use of protic solvents. This strategy allows the formation of a novel C-C bond between aldehydes and weakly nucleophilic and medicinally relevant heteroaryls such as indoles, pyrroles, indazoles, and azaindoles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kai Yang, Yukang Wang, Sanzhong Luo, Niankai Fu
Summary: In this study, we developed an electrophotochemical metal-catalyzed protocol for direct asymmetric decarboxylative cyanation of aliphatic carboxylic acids. By utilizing the synergistic merging of electrophotochemical cerium catalysis and asymmetric electrochemical copper catalysis, mild reaction conditions were achieved for the formation and utilization of carbon-centered radicals. This environmentally benign method smoothly converts a diverse array of arylacetic acids into the corresponding alkyl nitriles in good yields and enantioselectivities without using chemical oxidants or pre-functionalization of the acid substrates and can be readily scaled up.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Ebbin Joseph, Ian Smith, Jon A. Tunge
Summary: The selective incorporation of fluorine-containing groups adjacent to sterically hindered alkyl groups remains a challenge, but the cobalt-catalyzed method allows for the facile construction of difluoroalkylated products and late-stage functionalization of molecules of biological relevance.
Article
Chemistry, Multidisciplinary
Dong-Jin Jang, Sukhyun Lee, Juyeol Lee, Dohyun Moon, Young Ho Rhee
Summary: The study reports a Pd-catalyzed asymmetric addition reaction that leads to the synthesis of beta-substituted ketones in an asymmetric manner through a branch-selective decarboxylative allylation pathway. Various alkoxyallenes as well as amidoallenes can be used in this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Magdalena Tasic, Albert Ruiz-Soriano, Daniel Strand
Summary: This article describes a practical three-step approach to diareno[a,e]cyclooctatetraenes using an efficient copper(I) catalyzed double decarboxylation as the key step. The method relies on cheap and abundant reagents, can be performed on scale, and is also applicable to unsymmetrical derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kai Yang, Jiaqing Lu, Liubo Li, Sanzhong Luo, Niankai Fu
Summary: This method utilizes electrophotochemical dual metal catalysis to achieve decarboxylative arylation of simple aliphatic carboxylic acids with aryl halides, displaying mildness and robustness. Moreover, it can directly use simple primary aliphatic acids such as acetic acid as substrates, demonstrating significant research implications.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Shuling Yu, Chao Hong, Zhanxiang Liu, Yuhong Zhang
Summary: The addition of an inert vinylic C-H bond to formaldehyde has been achieved via cobalt-catalyzed C-H activation, leading to the production of gamma-hydroxymethylated butenolides. The unique reactivity of cobalt species compared to related Rh or Ir catalysts was observed in this process. Gamma-hydroxymethylated butenolides were synthesized by treating with Na2CO3 after the catalytic reaction in one pot.
Article
Chemistry, Multidisciplinary
Yin Yuan, Junfeng Yang, Junliang Zhang
Summary: In this study, a Cu-catalyzed enantioselective decarboxylative cyanation method via the merger of photocatalysis and electrochemistry was reported. This method provides an efficient and straightforward approach for decarboxylative coupling, eliminating the need for stoichiometric chemical oxidants or substrate prefunctionalization. Mechanistic insight on enantioselectivity control was obtained through DFT calculations.
Article
Chemistry, Organic
Shuling Yu, Chao Hong, Zhanxiang Liu, Yuhong Zhang
Summary: An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates was reported. The treatment of a variety of alkyl halides with a Na2CO3/MeOH solution could smoothly achieve 5-alkylation of the cyclopentenones. Excess formaldehyde and malonate led to a multicomponent reaction that afforded multisubstituted cyclopentenones through a Michael addition.
Article
Chemistry, Multidisciplinary
Jingjing Wang, Xue Liu, Ziyan Wu, Feng Li, Tingting Qin, Siyuan Zhang, Weiguang Kong, Lantao Liu
Summary: The silver-catalyzed decarboxylative C-H alkylation of cyclic aldimines with abundant aliphatic carboxylic acids has been achieved under mild reaction conditions, producing moderate to good yields (32%-91%). The study also demonstrated the potential of the technology in gram-scale reactions and late-stage modification of drugs.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Physical
Jiang-Lin Hu, Felix Bauer, Bernhard Breit
Summary: A novel ruthenium-catalyzed synthetic method for branched allylic esters via addition of carboxylic acids to allenes was reported in this study. Ligands based on the Josiphos skeleton were designed and prepared, achieving high yield and high enantiomeric excess. Deuterium labeling experiment was conducted to propose a plausible mechanism, and enantiopure lactones of five- and six-membered ring were synthesized through a RCM reaction of the branched allylic ester product.
Article
Chemistry, Organic
Qiuling Song, Fumei Ke, Changjiang Yu, Xin Li, Heyun Sheng
Summary: A convenient method for synthesizing fluorine-containing heterocyclic compounds was developed, involving copper-catalyzed free radical addition and molecular lactone exchange of alkynol and ethyl bromodifluoroacetate. This method offers easy availability of raw materials, good stereochemical selectivity, and simple operation. It also allows for the synthesis of valuable tetrasubstituted E-configurated alkenes and various vinyl C-Br bonds and difluoromethylene-containing functionalized heterocycles.
Article
Chemistry, Organic
Raphael K. Klake, Mytia D. Edwards, Joshua D. Sieber
Summary: A new catalytic enantioselective addition method utilizing copper-catalyzed reductive coupling to add N-substituted allyl equivalents to ketones has been developed, accessing important chiral 1,2-aminoalcohol synthons with high levels of regio-, diastereo-, and enantioselectivity. Factors affecting enantioinduction are discussed, including the identification of a reversible ketone allylation step previously unreported in copper-catalyzed reductive coupling.
Article
Chemistry, Multidisciplinary
Yong Luo, Yuanhong Ma, Zhaomin Hou
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Physical
Can Xue, Yong Luo, Huailong Teng, Yuanhong Ma, Masayoshi Nishiura, Zhaomin Hou
Article
Chemistry, Physical
Chunzhen Yang, Georgios Nikiforidis, Ji Young Park, Jonghoon Choi, Yong Luo, Liang Zhang, Shi-Cheng Wang, Yi-Tsu Chan, Jihun Lim, Zhaomin Hou, Mu-Hyun Baik, Yunho Lee, Hye Ryung Byon
ADVANCED ENERGY MATERIALS
(2018)
Article
Chemistry, Multidisciplinary
Yuanhong Ma, Shao-Jie Lou, Gen Luo, Yong Luo, Gu Zhan, Masayoshi Nishiura, Yi Luo, Zhaomin Hou
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Gu Zhan, Huai-Long Teng, Yong Luo, Shao-Jie Lou, Masayoshi Nishiura, Zhaomin Hou
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Physical
Yong Luo, Huai-Long Teng, Can Xue, Masayoshi Nishiura, Zhaomin Hou
Article
Chemistry, Multidisciplinary
Wenxuan Xu, Huailong Teng, Yong Luo, Shaojie Lou, Masayoshi Nishiura, Zhaomin Hou
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Shao-Jie Lou, Liang Zhang, Yong Luo, Masayoshi Nishiura, Gen Luo, Yi Luo, Zhaomin Hou
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Hao Ding, Wan-Ying Qi, Jing-Song Zhen, Qiuping Ding, Yong Luo
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Wan-Ying Qi, Jing-Song Zhen, Xiao-Hong Xu, Xian Du, Yi-Hui Li, Han Yuan, Yun-Shi Guan, Xun Wei, Zi-Ying Wang, Guohai Liang, Yong Luo
Summary: The study describes a base-mediated reaction for synthesizing geminal silylboronates with a benzylic proton under mild conditions, as well as achieving deaminative silylation of aryl ammonium salts. This strategy, featuring high efficiency, mild reaction conditions, and good functional group tolerance, provides efficient pathways for late-stage functionalization of amines.
Article
Chemistry, Organic
Xiao-Hong Xu, Jing-Song Zhen, Xian Du, Han Yuan, Yi-Hui Li, Man-Hei Chu, Yong Luo
Summary: A visible-light-mediated late-stage sulfonylation of anilines with sulfonamides under simple reaction conditions is demonstrated. Various primary or secondary sulfonamides, including several pharmaceuticals, were successfully incorporated through N-S bond activation and C-H bond sulfonylation. The synthetic utility of this strategy is highlighted by the construction of complex anilines bearing diverse bioactive groups.
Article
Chemistry, Physical
Jingsong Zhen, Xian Du, Xiaohong Xu, Yihui Li, Han Yuan, Dejing Xu, Can Xue, Yong Luo
Summary: A visible-light-mediated late-stage arylation of N-S bonds in sulfonamides has been developed using readily available imines as sulfonyl radical source. This methodology characterized by broad substrate scope and simple reaction conditions also has high atom economy.
Article
Chemistry, Organic
Xian Du, Jing-Song Zhen, Xiao-Hong Xu, Han Yuan, Yi-Hui Li, Yeqin Zheng, Can Xue, Yong Luo
Summary: Sulfonamides have many advantages and can be used to efficiently synthesize various complex sulfones by utilizing sulfonyl imines as sulfonyl radical precursors via visible-light irradiation.
Article
Chemistry, Organic
Jingsong Zhen, Yihui Li, Han Yuan, Xiaohong Xu, Xian Du, Xin-Qing Li, Yong Luo
Summary: In this study, visible-light-mediated cross-coupling of sulfonyl fluorides and aryl boronic acids in water was explored without the presence of transition metals, providing an efficient and environmentally-friendly method for the synthesis of diaryl sulfones. Sulfonyl fluorides, as stable and readily available sulfonyl radical sources, enable sulfone synthesis under mild reaction conditions with high functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Yong Luo, Hao Ding, Jing-Song Zhen, Xian Du, Xiao-Hong Xu, Han Yuan, Yi-Hui Li, Wan-Ying Qi, Bing-Zhe Liu, Shi-Man Lu, Can Xue, Qiuping Ding
Summary: This novel methodology achieves the sulfonylation of boronic acids with sulfonamides through visible light-mediated N-S bond cleavage, showing simplicity, good functional group tolerance, and high efficiency. Successful late-stage functionalization examples suggest a high potential utility in pharmaceutical science and organic synthesis.
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)
