Article
Chemistry, Organic
Feilong Sun, Chengxi Yang, Jie Ni, Gui-Juan Cheng, Xianjie Fang
Summary: A regiodivergent nickel-catalyzed hydrocyanation of 1-aryl-4-silyl-1,3-diynes is reported, where appropriate ligands result in high yields and regioselectivities of two different enynyl nitriles. DFT calculations show that different ligands lead to diverse alkyne insertion modes, impacting the regioselectivity. The synthetic value of cyano-containing 1,3-enynes is demonstrated through downstream transformations.
Article
Chemistry, Organic
Ran Ding, Ya-Li Liu, Hui Hao, Chuan-Yi Chen, Lei Liu, Nian-Shou Chen, Yu Guo, Pei-Long Wang
Summary: A copper(I)-catalyzed sulfonylation-cyclization method has been developed for the transformation of 1,5-dienes with sulfonyl chlorides. The reaction exhibits a wide substrate scope and excellent regioselectivity, resulting in the formation of derivatized 1,5-dihydro-2H-pyrrol-2-one scaffold in one pot.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Perla Bharath Kumar, Chittala Emmaniel Raju, Patel Hinal Chandubhai, Balasubramanian Sridhar, Galla V. Karunakar
Summary: Molecules obtained from nature have various biological applications in medicinal chemistry, agrochemicals, and material sciences. Oxygen-containing molecules such as chromenes and benzochromenes are found to have potential biological applications.
Article
Chemistry, Applied
Dan Wang, Junhui Lin, Yannan Zhu, You Huang
Summary: The study highlights the robustness of phosphine catalysis in enabling domino benzannulation reactions between allenoates and enamines. It demonstrates the synthesis of various substituted terephthalates under simple and practical reaction conditions. The reaction can be conducted on a gram scale with high yield, and the versatility of the terephthalate products is shown through various conversions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Ming Li, Guo-Qing Sun, Yu-Yu Liu, Shun-Xi Li, Hai-Chao Liu, Yi-Feng Qiu, Dong-Pin Chen, Xi-Cun Wang, Yong-Min Liang, Zheng-Jun Quan
Summary: A nickel-catalyzed three-component tandem radical cyclization reaction was developed to synthesize gamma-lactam-substituted allene derivatives from aryl bromides, 1,3-enynes, and aryl boric acids. This strategy allowed the lactam alkyl radicals generated through the cyclization process to participate in multicomponent coupling, leading to the direct conversion of 1,3-enynes into poly substituted allene compounds. The method demonstrated wide substrate scope and provided a series of 1,5-difunctionalized allenes in a one-pot reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chien-Chi Wu, Ram Ambre, Meng-Hsuan Lee, Jiun-Jie Shie
Summary: We present an efficient and mild tandem catalytic process for synthesizing functionalized pyrrole-3-carbaldehydes. This process involves a one-pot three-component reaction using 5-bromo-1,2,3-triazine, terminal alkynes, and primary amines, catalyzed by palladium for Sonogashira coupling, followed by annulation mediated by silver to access the multi-functionalized pyrrole-3-carbaldehydes.
Article
Chemistry, Organic
Rajendhiran Saritha, Sesuraj Babiola Annes, Karuppaiah Perumal, Bhaskaran Shankar, Subburethinam Ramesh
Summary: A simple approach to synthesize pyrazolo [1,5-a] quinoline thioether derivatives using dimethyl sulfoxide and iodine/ascorbic acid as catalysts is described. The compounds were identified using various analytical techniques, and a reasonable reaction mechanism was proposed based on control experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Andrea Cataffo, Miguel Pena-Lopez, Riccardo Pedrazzani, Antonio M. Echavarren
Summary: This study presents two classes of stereoselective cyclizations using a chiral auxiliary approach. The first class involves the stereoselective cascade cyclization of 1,5-enynes using Oppolzer camphorsultam as chiral auxiliary, leading to the synthesis of enantioenriched spirocyclic ketones. The second class focuses on the stereoselective alkoxycyclization of 1,6-enynes mediated by Evans-type oxazolidinone, resulting in the formation of enantioenriched beta-tetralones after removal of the auxiliary.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Chunxiang Pan, Gaowei Wang, Hengyuan Zhao, Jianxiao Ni, Ruifeng Fan, Yongyun Zhou, Yuanbin Zhu, Shiyuan Wu, Baomin Fan
Summary: An efficient stereoselective cobalt-catalyzed hydrovinylative cyclization of 1,6-enynes with chalcones to obtain functionalized pyrrolidines has been developed. The products were furnished in good yields with up to 93% ee. A plausible mechanism through which the transformation was initiated by cyclization of 1,6-enynes is proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Zhantao Yang, Zhiqiang Yu, Yulin He, Wei Feng, Yinchao Zhang, Junjie Wang, Xiangtao Kong, Chun-Hua Yang
Summary: A Rh-catalyzed regioselective, stereoselective carbocyclization/borylation reaction of acrylate-containing 1,6-enynes was developed, enabling the synthesis of versatile and densely functionalized pyrrolidine compounds. The reaction allows for the formation of pyrrolidines with either (Z) or uncommon (E) geometry at the double bond, depending on the substituent on the alkyne, with sterically hindered and conjugative aryl groups favoring the latter configuration. The reaction also leads to the formation of a tetrasubstituted vinyl boronate, containing an all-carbon quaternary stereocenter.
Article
Chemistry, Organic
Meng-Lian Yao, Xiao-Yuan Wang, Guang-Chao Feng, Ji-Kai Liu, Bin Wu, Jin-Ming Yang
Summary: A novel palladium(II)-catalyzed intramolecular [2 + 2 + 2] annulation of indolyl 1,3-diynes is described, resulting in the synthesis of various azepino-fused carbazoles in moderate to excellent yields. The success of this transformation is attributed to the use of a carboxylic acid additive. This method exhibits broad functional group tolerance, easy handling in air, and 100% atom economy. Additionally, the scalability, late-stage derivatization, and photophysical property investigations demonstrate the potential synthetic utility of this methodology.
Article
Chemistry, Multidisciplinary
Galla Karunakar, Chittala Emmaniel Raju, Gottam Sreenivasulu, Perla Bharath Kumar, Veerabhushanam Kadiyala, Balasubramanian Sridhar
Summary: An efficient intramolecular cyclization reaction was developed to synthesize indenone derivatives. The gold-catalyzed organic transformation allowed the conversion of substituted 1,5-diyenes to the corresponding indenones, resulting in the formation of two C=O and one C-C bonds in one pot under mild reaction conditions, leading to moderate to excellent yields of the target molecules.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Aureilien Dupeux, Emilie Gentilini, Veironique Michelet
Summary: Gold-catalyzed Prins-type cyclizations are a fascinating approach for synthesizing complex molecules with excellent stereochemistry. Researchers have developed a new and efficient system for this reaction, achieving yields up to 89% in 13 examples. They also reported the first enantioselective version of a gold-catalyzed Prins-type cyclization using a chiral TADDOL-based Au(I) phosphonite complex, yielding highly enantiomerically enriched products (>99% ee) after crystallization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
William G. Shuler, Sai P. Parvathaneni, Jacob B. Rodriguez, Taylor N. Lewis, Adam J. Berges, Christopher J. Bardeen, Michael J. Krische
Summary: A novel benzannulation reaction catalyzed by ruthenium was used to synthesize a new derivative of rubicene with unique packing structure, and their photophysical properties were studied.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Si-Hua Hou, Xuan Yu, Rui Zhang, Cole Wagner, Guangbin Dong
Summary: This article describes the development of Rh(I)-catalyzed intramolecular annulations for constructing complex C(sp3)-rich scaffolds. Different catalysts exhibit divergent reactivities and achieve excellent diastereo- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
