Correction
Chemistry, Organic
Zhifei Zhao, Prasanta Ray Bagdi, Shuang Yang, Jinggong Liu, Andrej Emanuel Cotman, Weici Xu, Xinqiang Fang
Article
Chemistry, Organic
Rui Liu, Shuang Yang, Zhizhou Chen, Xiangwen Kong, Houqiang Ding, Xinqiang Fang
Article
Chemistry, Applied
Shouang Lan, Hao Zhang, Zhizhou Chen, Shuang Yang, Xinqiang Fang
Summary: A unique cascade sequence using dienone substrates was reported for the first time, allowing rapid construction of 5/6/5 fused ring compounds with good to high stereoselectivities under mild conditions. Enantioenriched polycyclic rings can be obtained with high enantioselectivity using ruthenium-catalyzed transfer hydrogenation, providing a concise approach for the construction of related fused ring substances.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Qi Zhang, Deb Kumar Das, Shuang Yang, Yao Fu, Xinqiang Fang
Summary: The mechanism of N-heterocyclic carbene-catalyzed umpolung of beta,gamma-unsaturated alpha-diketone was found to be more complicated than originally proposed, involving nucleophilic O-acylated homoenolate and electrophilic alpha,beta-unsaturated acyl azolium intermediates. Both DFT calculations and experimental studies confirmed the existence of these key intermediates, leading to a revised mechanism for product formation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shouang Lan, Rui Liu, Xiangwen Kong, Jinggong Liu, Benlong Luo, Shuang Yang, Xinqiang Fang
Summary: A unique deoxygenative cyclodimerization of alkynyl 1,2-diketones facilitated by Ti((OPr)-Pr-i) (4) has been achieved, resulting in a series of highly functionalized furan products. Unusual C-C and C=O bond cleavage of the substrates is observed, with Ti(OiPr)(4) playing triplicate roles in the reaction. Furthermore, the products exhibit uncommon fluorescent emission in the solid state, indicating potential practical applications of this work.
Article
Chemistry, Organic
Zhizhou Chen, Xiangwen Kong, Shengtong Niu, Shuang Yang, Jinggong Liu, Bolai Chen, Benlong Luo, Changyu Zhou, Chenglin Ding, Xinqiang Fang
Summary: Asymmetric construction of cyclopentenones using N-Heterocyclic carbene catalysis with enals and alpha-diketones has been achieved, yielding a series of highly functionalized cyclopentenones in a highly diastereo- and enantioselective manner. The protocol is tolerant of substrates with both aromatic and aliphatic groups, and further transformations of the products have led to a range of value-added molecules.
Article
Multidisciplinary Sciences
Shengtong Niu, Hao Zhang, Weici Xu, Prasanta Ray Bagdi, Guoxiang Zhang, Jinggong Liu, Shuang Yang, Xinqiang Fang
Summary: The article introduces the rationale, scope, and applications of the kinetic resolution of auxiliary adjacent alcohols (KRA*) strategy to overcome the challenges faced by contemporary asymmetric catalysis, allowing for the synthesis of optically enriched compounds with two, three, or four spatially and electronically similar groups.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Syeda Tazeen Zehra, Shouang Lan, Hao Zhang, Jinggong Liu, Shuang Yang, Xinqiang Fang
Summary: Developing a general method for obtaining optically pure fully substituted carbon molecules with various fluorinated groups is important but challenging. In this study, we demonstrate that by using secondary OH as a kinetic resolution auxiliary group, previously unavailable fluorinated fully substituted carbon molecules can be obtained with excellent enantioselectivities, providing an alternative solution to the limitations of known methods.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Shengtong Niu, Yingkun Luo, Chao Xu, Jinggong Liu, Shuang Yang, Xinqiang Fang
Summary: In this work, a general protocol for copper-catalyzed allylic substitutions using stable soft nucleophiles has been developed, resulting in the synthesis of highly selective functionalized 1,3- and 1,4-enynes. Mechanistic studies propose a copper acetylide-bonded allylic cation as the key intermediate, featuring an outer-sphere nucleophilic attack. The demonstrated diversified reactivities in this study will inspire further exploration.
Article
Chemistry, Physical
Fan Gong, Xiangjian Meng, Shouang Lan, Jinggong Liu, Shuang Yang, Xinqiang Fang
Summary: The merger of asymmetric semipinacol-type rearrangement and transition-metal-catalyzed propargylic alkylation has successfully produced enantioenriched cyclo- and heterocyclopentanones with alpha-alkynylated quaternary stereocenters. These products are challenging to obtain using other methods and have demonstrated their synthetic value in further transformations. This work introduces a distinctive mode of inducing asymmetric 1,2-carbon migration and expands the scope of propargylic substitution.
Article
Chemistry, Organic
Ting Chen, Fan Gong, Sakkani Nagaraju, Jinggong Liu, Shuang Yang, Xingkuan Chen, Xinqiang Fang
Summary: In this work, the I-2-catalyzed oxa-Nazarov cyclization-Michael addition cascade between vinyl alpha-diketones and enones has been developed, providing a range of functionalized dihydrofuranones with good to high yields. Further transformations on the products have also been achieved. Mechanistic studies reveal the simultaneous occurrence of 1,2-hydride shift during dihydrofuranone formation.
Article
Chemistry, Multidisciplinary
Chao Xu, Hao Zhang, Shouang Lan, Jinggong Liu, Shuang Yang, Qi Zhang, Xinqiang Fang
Summary: Transition-metal-catalysed reactions of cyclic ethynylethylene carbonates have been extensively investigated due to their robustness in forming new bonds and constructing diverse molecules. A novel reaction pattern is reported, where cyclic ethynylethylene carbonates firstly undergo rearrangement to release allenal intermediates, which then react with various nucleophiles to produce synthetically useful allylic and propargylic allenols, phosphorus ylides, and cyclopropylidene ketones through an addition process rather than substitution pathway. The products allow for further transformations, and mechanistic studies reveal that the reaction proceeds via base-mediated deprotonation as the key step to induce the rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Lei Yang, Xinchao Wang, Meng Zhang, Shangda Li, Xinqiang Fang, Gang Li
Summary: This study reports a Pd-catalyzed remote isodesmic meta-C-H iodination of phenethylamines, benzylamines, and 2-aryl anilines using 1-iodo-4-methoxy-2-nitrobenzene as the mild iodinating reagent. A range of valuable meta-iodinated and even multi-halogenated amines were successfully synthesized, paving the way for synthetic chemists to access various amine derivatives at the challenging meta-positions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Li Chen, Shengtong Niu, Shouang Lan, Wenjun Liu, Shuang Yang, Xinqiang Fang
Summary: Two unprecedented trifunctionalization reactions of ynones have been achieved using organic phosphine catalysis under mild and environmentally benign conditions. By using (PrOH)-Pr-i as the solvent, a range of valuable compounds were synthesized with high stereoselectivity. Uncommon bond cleavage and formation processes were observed, demonstrating the robustness of organocatalysis in facilitating complex transformations.
