Article
Chemistry, Physical
Bo-Han Zhu, Ying-Qi Zhang, Hao-Jin Xu, Long Li, Guo-Cheng Deng, Peng-Cheng Qian, Chao Deng, Long-Wu Ye
Summary: An efficient copper-catalyzed tandem alkyne hydration/intramolecular Mannich reaction has been investigated for the synthesis of valuable compounds. This method allows the efficient synthesis of 3,4-dihydro-2-quinolones with high regio-, diastereo-, and enantioselectivity.
Article
Chemistry, Multidisciplinary
Nengneng Zhou, Qiankun Xu, Ziqin Xia, Kaimo Kuang, Sixin Wu, Wenping Li, Man Zhang
Summary: In this study, a novel palladium-catalyzed radical cascade reaction was developed for the synthesis of cyanoalkylsulfone-containing cyclopenta[gh]phenanthridines. The reaction involved the cleavage of a C-C single bond and insertion of SO2, and showed mild reaction conditions, a broad substrate scope, and high functional group tolerance.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Yin Xu, Gan-Lu Qian, Da-Qiu Cui, Peng-Cheng Qian, Chao-Yue Zhao, Xin Hong, Bo Zhou, Long-Wu Ye
Summary: Herein, a chiral Bronsted acid-catalyzed desymmetrization reaction of diynes is reported, providing a facile access to enantioenriched 1,3-diaminopropanol derivatives and γ-butyrolactones with high enantioselectivities. These products can be used as precursors for the synthesis of versatile N- and O-heterocycles, which are important structural cores of bioactive molecules. Control experiments and theoretical calculations are used to confirm the mechanism and elucidate the origin of enantioinduction.
Article
Chemistry, Physical
Lin-Jun Qi, Chong-Yang Shi, Peng-Fei Chen, Long Li, Gang Fang, Peng-Cheng Qian, Chao Deng, Jin-Mei Zhou, Long-Wu Ye
Summary: The study presents a novel gold-catalyzed 1,1-carboalkoxylation method for the synthesis of valuable cyclic compounds, enabling asymmetric synthesis through a chirality-transfer strategy. Further mechanistic insight into the distinct migration into gold carbenes is supported by theoretical calculations.
Article
Chemistry, Multidisciplinary
Shangbiao Zhang, Yan Gao, Rui Xiao, Yang Li, Yanan Wang, Zheliang Yuan
Summary: In this study, a tandem synthesis of various CF3Se-containing heterocyclic compounds was developed using Tf2O as the catalyst and trifluoromethyl selenoxides as the electrophilic trifluoromethylselenolation reagents. The process is characterized by its mild conditions, easy operation, and good functional group compatibility. A variety of alkynes were successfully transformed into CF3Se-containing indoles, benzofurans, benzothiophenes, isoquinolines, and chromenes in good yields.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Organic
Jumreang Tummatorn, Somsak Ruchirawat, Charnsak Thongsornkleeb
Summary: Halogenative annulation of alkyne-tethered N- and O-containing arenes is a general strategy for constructing various halogenated N- and O-heterocycles. This method provides valuable synthetic building blocks carrying C(sp2)- halide functional groups, which are useful for cross-coupling reactions and other transformations. This Short Review examines different halogenative annulation methods for constructing aryl-fused halogenated N- and O-heterocycles, with a focus on recent technologies and the roles of halogenating agents.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Gilson Zeni, Benhur Godoi, Carla K. Jurinic, Andrei L. Belladona, Ricardo F. Schumacher
Summary: This manuscript provides an overview of the most recent advances in the synthesis of carbo- and heterocycles through reactions of alkynes with organyl chalcogenides under metal-free conditions. Methods discussed include the use of electrophilic chalcogenyl halides and radical cyclization protocols utilizing electrochemical oxidative conditions, light-induced photoredox catalysis, or mild oxidants.
Article
Chemistry, Organic
Leilei Cao, Liliang Huang, Xianjun Xu, Erik V. Van der Eycken, Huangdi Feng
Summary: A novel method for the construction of nitrogen-tethered 1,6-enynes with high atom economy and exclusive chemoselectivity has been developed. Experimental studies suggest that the key step in this methodology is the alkyne-iminium ene reaction involving an intermolecular hydride transfer.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Guang-Yu Zhu, Ji-Jia Zhou, Li-Gao Liu, Xiao Li, Xin-Qi Zhu, Xin Lu, Jin-Mei Zhou, Long-Wu Ye
Summary: A catalyst-dependent [3,3]-sigmatropic rearrangement of sulfoxide-ynamides has been described, enabling the divergent and atom-economic synthesis of valuable medium-sized N,S-heterocycles with moderate to good yields and broad substrate scope. Excellent enantioselectivities have been achieved via an unprecedented chirality-transfer. Theoretical calculations have been employed to elucidate the origins of the catalyst-dependent stereospecific [3,3]-rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Guang'an Zhang, Yonghong Pei, Junwei Wang, Xinyu Zhu, Zhongxian Li, Fengqian Zhao, Junliang Wu
Summary: A highly atom-economical strategy has been developed for the synthesis of chiral propargylic cyanides using a chiral copper complex catalyst. Propargylic radicals are smoothly obtained through direct decarboxylation of propargylic carboxylic acids, with excellent selectivity and functional group compatibility. Gram-scale reactions and conversion reactions demonstrate the synthetic value of this strategy.
Article
Chemistry, Organic
Angelica R. Claus, Tales A. C. Goulart, Davi F. Back, Gilson Zeni
Summary: In this study, a regio- and stereoselective synthesis of alpha-methylene-beta-lactams was reported via a 4-exo-dig-cyclization of N-benzyl-N-methyl-propiolamides catalyzed by a base. Experimental evidence suggests that the transformation proceeds through a concerted ionic cyclization, followed by protonation of the vinyl species promoted by tert-butanol. The obtained alpha-methylene-beta-lactams were suitable substrates for the Heck coupling conditions, leading to the formation of corresponding products through carbon-carbon bond formation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Marina Yu. Dvorko, Dmitrii A. Shabalin, Igor A. Ushakov, Elena Yu. Schmidt, Boris A. Trofimov
Summary: The cascade dimerization of alkynones with sterically hindered secondary alkyl groups at the carbonyl function unexpectedly produced highly functionalized furans. This reaction efficiently takes place at room temperature in the presence of a potassium tert-butoxide/dimethylsulfoxide superbase catalytic system. Alkynones with an additional C-H active site at the carbon-carbon triple bond followed a different dimerization pathway to form 3-alkenylpyran-4-ones. The discovery of these reactions expands the traditional understanding of alkynone reactivity in strong basic conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Hayeon Kwak, Eunsu Kang, Jae Yeong Song, Geunhee Kang, Jung Min Joo
Summary: The development of modular approaches for heteroaromatic cores and substituents is crucial for drug candidates and organic functional materials. A new strategy involving the cyclization of heteroarenes tethered with alkynes through a norbornene bridge was developed. The Pd catalytic system transformed a variety of five-membered heteroarenes to the corresponding benzofused products, demonstrating its versatility in the annulation of (hetero)aromatic rings.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Applied
Xian-Rong Song, Ruchun Yang, Qiang Xiao
Summary: Significant progress has been made in recent years in the construction of heterocyclic compounds using propargylic alcohols, with reactions divided into four categories based on different types of nucleophiles to capture allenyl carbocation.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Hong Zhang, Jieyin He, Wendi Xu, Liangliang Yang, Xue Zhang, Haiyang Wang, Ming Lang, Jian Wang, Shiyong Peng
Summary: A copper-catalyzed cascade reaction between 1,6-enynes and sulfoxonium ylides, leading to the formation of structurally intriguing 2,3-disubstituted indolines, has been reported. The reaction exhibited moderate to excellent yields and good chemo-, regio-, and diastereoselectivities under mild reaction conditions. Notably, the reactivity of sulfoxoniumylide-derived copper-carbene was found to be different from that of diazo copper-carbene. The proposed mechanism involves the formation of an initial ammonium ylide rather than an allene.