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, Organic
Xianjun Xu, Huangdi Feng, Erik V. Van der Eycken
Summary: An efficient synthesis route for unsymmetric 1,4-diamino-2-butynes has been developed using a microwave-assisted Cu(I)-catalyzed cross-A(3)-coupling/decarboxylative coupling process. The multicomponent reaction yields target products in moderate to good yields with high chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ge Wu, Xueying Zhou, Caihong Wang
Summary: A novel and efficient method for decarboxylative alkynylselenation of indoles using Se powder and propiolic acids as catalyst has been developed. This method avoids the use of prefabricated arylselenation reagent and over-seleniumation issues and enriches the chemistry of selenium powder. Furthermore, this reaction can be extended to pyrrole, and its practical utility has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Sakamuri Sarath Babu, Purushothaman Gopinath
Summary: Photoredox-mediated tandem addition-chemoselective cyclization has been used for the synthesis of sulfonyl and activated alkyl-decorated dihydroquinazolinones. Selective N-cyclization was achieved in the presence of more reactive amidic oxygen, through careful choice of starting materials. The versatility of the methodology was demonstrated with various sulfonyl chlorides and activated alkyl halides, and the synthetic utility of the method was showcased through large-scale synthesis of sulfonyl-substituted dihydroquinazolinone.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jiangwei Wen, Xue Sun, Kelu Yan, Tingtao Yan, Zhen Liu, Yang Li, Jianjing Yang
Summary: In this study, a simple and practical method for achieving decarboxylative phosphorylation of N-aryl glycines to obtain alpha-amino phosphine oxides under visible-light photoredox catalysis was presented. This method demonstrated high efficiency and excellent tolerance towards functional groups, and can be easily scaled up under extremely mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Ying Chen, Sailuo Li, Lanting Xu, Dawei Ma
Summary: N-1-(2,6-Dimethylphenyl)-N-2-(pyridin-2-ylmethyl)-oxalamide (DMPPO) was found to be a more effective ligand for copper-catalyzed coupling reaction than previously reported ones. Only 3 mol % CuCl and DMPPO are needed for complete coupling at 100 degrees C (for bromides) and 80 degrees C (for iodides). Both (hetero)aryl and alkyl substituted 1-alkynes showed good reactivity, resulting in the formation of diverse internal alkynes.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Shuaishuai Wang, Tingrui Li, Chengyihan Gu, Jie Han, Chuan-Gang Zhao, Chengjian Zhu, Hairen Tan, Jin Xie
Summary: This article reports on an iron-catalyzed reaction for efficient construction of aromatic tertiary amines, which is important in drug discovery and organic chemistry. The reaction employs a radical tandem C-N coupling strategy and can synthesize nonsymmetric aromatic tertiary amines under mild conditions.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Organic
Ruchi Sharma, M. Ramu Yadav
Summary: Decarboxylative coupling reactions using readily available (hetero)aryl carboxylic acids are an efficient approach for forming new C-C and C-X bonds, with the advantage of eliminating CO2 as a by-product and being more environmentally friendly. This review summarizes recent developments in ipso-decarboxylative C-X bond formations using (hetero)aryl carboxylic acids, and highlights current limitations and future research opportunities in aryl-decarboxylative coupling reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Applied
Manjunath S. Lokolkar, Pravin A. Mane, Sandip Dey, Bhalchandra M. Bhanage
Summary: This study presents Xantphos-coordinated palladium dithiolate complexes as catalysts for decarboxylative Sonogashira coupling reaction, showing high catalytic activity and recyclability. In situ generation of palladium nanoparticles plays a crucial role in the reaction.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Huihui Kong, Lena Viergutz, Lacheng Liu, Alexander Sandvoss, Xinchen Peng, Henning Klaasen, Harald Fuchs, Armido Studer
Summary: Aryl propiolic acids can be used as new monomers in on-surface chemistry to synthesize poly(arylenebutadiynylenes) via decarboxylative Glaser coupling. Compared to aryl alkynes, the decarboxylative coupling occurs at slightly lower temperature and with better selectivity. The activation of propiolic acids is achieved through decarboxylation, while the classical Glaser coupling involves alkyne C-H activation and shows poor selectivity. The successful polymerization of bis(propiolic acids) as monomers demonstrates the efficiency of the decarboxylative coupling. Additionally, the new activation mode is compatible with aryl bromide functionalities, allowing the formation of unsymmetric metal-organic polymers on the surface through chemoselective sequential reactions.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Physical
Daiene de P. Lapa, Luana G. de Souza, Edgar Schaeffer, Eunice C. de Jesus, Andre A. Vieira, Alcides J. M. da Silva
Summary: A fast tandem reaction was used to synthesize a series of novel 1,4-naphthoquinones fused with specific N -O isoxazole, with moderate yield (up to 62%). The compounds were characterized by NMR, GC-MS, and ESI-HRMS. Computational analyses revealed the superior stability and polarizability of the N-O isomers, supporting the importance of this study and their potential biological activity.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Review
Chemistry, Applied
Cairong Wang, Ge Qiu, Chen Li, Kai Sun, Zhichuan Wang, Xin Wang
Summary: Carboxylic acid compounds are important structural units that exist widely in nature, and decarboxylative reactions have great significance in synthetic chemistry due to the non-flammable, non-toxic, and easy-to-remove byproduct carbon dioxide. Heterocyclic compounds are important backbones of various biologically active molecules, making research on new synthetic tactics for heterocyclic derivatives based on decarboxylative cyclization of great interest.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Abdol R. Hajipour, Shaghayegh Sadeghi Malek
Summary: A cobalt-NHC nanocatalyst was prepared and successfully applied for Suzuki and Sonogashira coupling reactions with high efficiency and recyclability. The use of green reaction conditions and replacing expensive palladium with earth-abundant cobalt makes this approach promising for sustainable chemistry.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Organic
Fang-Yuan Nie, Yi-Ping Cai, Qin-Hua Song
Summary: In this paper, a photocatalyst-free and visible light-driven decarboxylative alkylation of pyridinaldehydes is developed. The reactions are initiated by photoinduced single electron transfer and successfully convert pyridinaldehydes and 2-quinolinaldehydes to the corresponding ketones. Besides, this method also enables two other transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chiara Palladino, Tommaso Fantoni, Lucia Ferrazzano, Alessandra Tolomelli, Walter Cabri
Summary: This study described the development of sustainable and efficient aryl halides with copper-free Heck-Cassar-Sonogashira (HCS) and Suzuki-Miyaura (SM) cross-coupling reactions. The use of N-hydroxyethylpyrrolidone (HEP)/water as solvents and sodium 2'-dicyclohexylphosphino-2,6-dimethoxy-1,1'-biphenyl-3-sulfonate (sSPhos) as a ligand produced the target products with high turnover number (TON), high reaction mass efficiency (RME), and low process mass intensity (PMI). The optimal conditions for HCS and SM coupling reactions were determined, and the achieved PMI and RME were among the best in the field, simplifying purification processes crucial for industrial applications.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Xiang Li, Ruihong Zhang, Xiaofei Zhang, Peiyuan Zhu, Tuanli Yao
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Organic
Xiaofei Zhang, Peiyuan Zhu, Ruihong Zhang, Xiang Li, Tuanli Yao
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Conghui Zu, Tingfang Zhang, Fan Yang, Yusheng Wu, Yangjie Wu
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Mengxue Pei, Conghui Zu, Zhen Liu, Fan Yang, Yangjie Wu
Summary: This study successfully achieved the C4-H sulfamidation of 1-naphthylamine derivatives with NHSI catalyzed by copper(I) under mild conditions, yielding moderate to good results. Control experiments suggested that the visible-light-promoted reaction might proceed through a single-electron-transfer process, and preliminary DFT studies on intermediates supported the plausible mechanism, with the C4 site in the naphthyl ring identified as the most likely electrophilic reactive site.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Lixiao Zhao, Mengmeng Sun, Fan Yang, Yangjie Wu
Summary: An efficient method for silver-promoted direct C-H phosphonation of 1-naphthylamine derivatives with H-phosphonates was described, providing a facile route to 4-phosphonated 1-naphthylamine derivatives with tolerance to various functional groups. Further functionalization at different sites, such as fluoridation, methylation, methoxylation, and amination, was explored. DFT studies revealed the most electrophilic reactive site at the C4 position in the naphthyl ring.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiang Li, Qing Zhao, Yang Shen, Ran Ma
Summary: A highly efficient Rh(III)-catalyzed C-H diamidation and diamidation/intramolecular cyclization of N-iminopyridinium ylides with dioxazolones has been developed, providing diamidated products and benzoxazinone products in good to excellent yields. Notably, the tunable selectivity of this reaction can be controlled by simply switching the solvent and the temperature. This reaction features operational simplicity, a broad substrate scope, and a good functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiang Li, Danlu Li, Xiaofei Zhang
Summary: A Ru(ii)-catalyzed C-H bond activation/annulation reaction of N-iminopyridinium ylides with sulfoxonium ylides has been developed for the synthesis of diverse functionalized isocoumarin derivatives. This method shows broad substrate scope, excellent functional group tolerance, simple operation, and silver salt-free conditions. Furthermore, the utility of this method is demonstrated by the alkenylation of the product and efficient synthesis of biologically active thunberginol A.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiang Li, Yang Shen, Guodong Zhang, Xin Zheng, Qing Zhao, Zihe Song
Summary: A Ru(II)-catalyzed synthesis method has been developed for the efficient formation of dibenzo[b,d]furans and NH-free carbazolones. The reaction shows mild conditions, low catalyst loading, and broad substrate compatibility. Hydroxy and free amino groups were found to be effective directing groups.
Article
Chemistry, Multidisciplinary
Guodong Zhang, Ye Tian, Chengyu Zhang, Xiang Li, Feng Chen
Summary: Herein, a new decarboxylative Minisci-type reaction of N-heteroarenes with silanecarboxylic acids under photo- or silver-mediated conditions is reported. This C-H silylation strategy provides efficient access to diverse N-heteroarylsilanes in moderate to excellent yields with high regioselectivity, among which Ag-catalysed decarboxylation of silanecarboxylic acids furnishes an unprecedented method for silyl radical generation.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Cancan Feng, Luqing Tang, Fan Yang, Yangjie Wu
Summary: In this study, we reported a copper-catalyzed carbonyl-assisted hydroboration of terminal aliphatic alkenes with Markovnikov regioselectivity, using readily available and stable B(2)Pin(2) as the boron source. The reaction showed smooth progress with exclusive Markovnikov regioselectivity, providing easy access to a range of branched secondary alkyl boronic esters in moderate to excellent yields. The solvent was demonstrated to be the source of hydrogen, as confirmed by the deuterium experiments.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Xiaofei Zhang, Yao Wang, Jiaxin Liu, Chengpeng Tian, Xiang Li, Pan Xie, Zhenyu Zhu, Tuanli Yao
Summary: A visible-light-induced radical reaction was reported, which constructs 3-aminotetrahydro-1H-carbazoles through a cascade reaction between 2-alkenylarylisocyanides and cyclopropylanilines, achieving high atom and step economy.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Lihua Cao, Peisong Wang, Suyan Sun, Fan Yang, Yangjie Wu
Summary: A simple and efficient ruthenium-catalyzed C4-H bond cyanoalkoxylation protocol has been developed, which provides an efficient method for preparing cyano group-containing compounds with broad functional group tolerance and regioselectivity. The obtained products have significant potential value in organic synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yucong Sun, Cancan Feng, Peisong Wang, Fan Yang, Yangjie Wu
Summary: A facile and efficient cobalt-catalyzed regioselective C8-H sulfonylation of 1-naphthylamine derivatives with sodium sulfinates is described, resulting in moderate to good yields of sulfonylated naphthylamines. The reaction exhibits broad functional group tolerance and high regioselectivity, with the addition of a catalytic amount of NFSI or Selectfluor as an auxiliary ligand enhancing efficiency. The picolinamide moiety as a bidentate directing group likely plays a key role in this regioselective transformation.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Xiang Li, Ruihong Zhang, Yaoting Qi, Qing Zhao, Tuanli Yao
Summary: A highly efficient process for Rh(iii)-catalyzed C-H activation/annulation of N-iminopyridinium ylides with alkynes and diazo compounds has been achieved, providing a variety of isoquinolones and isocoumarins in moderate to excellent yields. This reaction features mild conditions, operational simplicity, broad substrate scope, and good functional group tolerance, with N-iminopyridinium ylide acting as an internal oxidant with alkynes and a leaving group with diazo compounds.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yaqi Shi, Fan Yang, Yangjie Wu
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
