Article
Chemistry, Multidisciplinary
Jia-Hao Xie, Chao Zheng, Shu-Li You
Summary: A novel Pd-catalyzed method for dearomative methoxyallylation of 3-nitroindoles with allyl carbonates has been developed, achieving high yields and diastereoselectivity. The method demonstrates good scalability and practicality with relatively low catalyst loading. Kinetic experiments suggest that the nucleophilic attack of the alkoxide anion is the rate-determining step in this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Madhawee K. Arachchi, Hien M. Nguyen
Summary: A broadly applicable methodology has been developed for the regio- and enantioselective construction of branched allylic carbon-heteroatom bonds from racemic, secondary allylic trichloroacetimidates. The products containing allylic C-O, C-N, and C-S bonds are obtained in synthetically useful yield and selectivity. Additionally, the chiral diene-ligated iridium catalyst is effective at promoting asymmetric aminations of acyclic secondary anilines.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Zeng-Hua Wu, Huai-Yu Wang, Huai-Lan Yang, Li-Hua Wei, Tamio Hayashi, Wei-Liang Duan
Summary: An iridium-catalyzed asymmetric synthesis of branched allylic phosphine compounds with excellent stereoselectivity and regioselectivity is reported. The use of phosphine sulfides with low deactivation capacity is crucial for the success of this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Pusu Yang, Rui-Xiang Wang, Yuan-Zheng Cheng, Chao Zheng, Shu-Li You
Summary: This study describes an iridium-catalyzed asymmetric allylic benzylation reaction under light irradiation. 2-methylbenzophenone derivatives were activated by ultraviolet light, enabling high enantioselectivity without the use of strong bases or pre-activation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jiadong Chen, Yulu Zhang, Shengbiao Tang, Ying Shao, Jiangtao Sun
Summary: This article presents the first example of C5-regioselective esterification of unactivated dienyl alcohols using free carboxylic acids as nucleophiles. The reaction, conducted under mild conditions, provides a series of 1,3-dienyl-5-ester compounds with excellent regioselectivity and E-selectivity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Rodney A. Fernandes, Ashvin J. Gangani, Arpita Panja
Summary: An efficient method using Pd-catalyzed reactions has been developed for the synthesis of 5-vinyl-2-isoxazolines, which can be further elaborated into various value-added products.
Article
Chemistry, Multidisciplinary
Xi-Jia Liu, Wen-Yun Zhang, Chao Zheng, Shu-Li You
Summary: Herein, an Ir-catalyzed asymmetric allylic substitution reaction of methyl azaarenes is reported. The reaction exhibits high yields and enantioselectivity, and utilizes the Knochel reagent for the formation of benzylic nucleophiles without additional activating reagents. The synthetic utility of this method has been demonstrated by an enantioselective synthesis of an allosteric protein kinase modulator.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yaomei Liu, Rui Chen, Lishuai Lu, Dengyu Yin, Fangpei Yan, Xiao-Xuan Li, Hua Xiao, Shilu Fan, Yi-Si Feng
Summary: An efficient copper-catalyzed cross-coupling method was developed for C-(sp(3))-CHF bond formation using allyl phosphate and 2-fluoro-2-(trimethylsilyl) acetate. Under moderate conditions, the reaction showed high conversion and provided a series of monofluoro-alkylation products in good yields, highlighting its practicality for gram-scale reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yibo Chen, Zhenbo Gao
Summary: A novel method has been developed for the mild and efficient synthesis of allyl sulfides using allyl alcohols and thiols as substrates, with Sn(OTf)(2) as a catalyst. The method allows for the synthesis of a diverse range of allyl sulfides, including linear and cyclic derivatives, with good yields. This approach shows high efficiency, with gram-scale reactions achieving over 90% yields using just 1 mol% catalyst.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Pusu Yang, Chen-Xu Liu, Wen-Wen Zhang, Shu-Li You
Summary: Indolizine is an important N-containing heterocyclic nucleus, and their derivatives exhibit interesting biological activities. However, asymmetric synthesis of indolizine derivatives has been rarely reported.
ACTA CHIMICA SINICA
(2021)
Article
Chemistry, Physical
Woo-Ok Jung, Binh Khanh Mai, Minjin Yoo, Samuel W. J. Shields, Jason R. Zbieg, Craig E. Stivala, Peng Liu, Michael J. Krische
Summary: The mechanism of pi-allyliridium C,O-benzoate-catalyzed allylic amination was studied using various methods. The reaction showed first-order dependence on catalysts and fractional-order dependence on amines. The intervention of cesium-bridged amine dimers and the formation of cesium amide nucleophiles were observed.
Article
Chemistry, Organic
Panchi Guo, Miao Zhan
Summary: A newly developed iridium-catalyzed enantioconvergent coupling reaction allows for the synthesis of various chiral homoallylic organoboronic esters with good yields and excellent enantioselectivities. The synthetic practicality of the products was demonstrated by their conversion to other useful families of compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yinan Ai, Hanlin Yang, Chunying Duan, Xingwei Li, Songjie Yu
Summary: A new Co-catalyzed sequential C-C and C-F activation of gem-difluorinated cyclopropanes has been developed, allowing the formation of nucleophilic fluoroallylcobalt, followed by addition to aldehydes to yield linear (Z)- and (E)-fluorinated homoallylic alcohols. This discovery established a new strategy for the efficient transformation of gem-difluorinated cyclopropanes and synthesis of challenging fluorinated homoallylic alcohols.
Article
Chemistry, Organic
Renren Li, Haocheng Zhang, Bangkui Yu, Hanmin Huang
Summary: A novel palladium-catalyzed cascade annulative aminomethylamination of diene-tethered enynes with aminals is reported. This method allows for the efficient synthesis of functionalized benzofulvenes with excellent chemo- and regioselectivities, as well as high atom economy. Mechanistic studies reveal the preferential reaction of alkylpalladium species with 1,3-enyne over 1,3-diene in initiating the cyclizative aminomethylamination.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Rodney A. Fernandes, Naveen Chandra, Ashvin J. Gangani, Gulenur N. Khatun
Summary: An efficient method for the synthesis of (E)-(3-alkoxybut-1-enyl)benzenes has been developed via Pd-catalyzed regioselective intermolecular hydroalkoxylation of 1-arylbutadienes. This method offers a simple operation, without the need for dry reaction conditions, and shows good tolerance to various substrates. The presence of chloromethyl methyl ether (MOMCl) as an additive is crucial to the success of the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
