Article
Chemistry, Organic
Jin-He Na, Xiang Liu, Jia-Wen Jing, Jing Wang, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A step-economical and efficient one-pot reaction was developed for the direct cross-coupling of aryl fluorosulfate with aryl bromide. This reaction, conducted at room temperature in THF solvent, does not require the use of preprepared/commercial organometallic reagents. By utilizing nickel catalyst, magnesium turnings, and lithium chloride, the desired biaryls were obtained in moderate to good yields with reasonable functional group compatibility.
Article
Chemistry, Multidisciplinary
Zhi-Peng Bao, Xiao-Feng Wu
Summary: This article develops an efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of 2-cyano-N-acetamide and 2-cyanoacetate compounds. The reaction proceeds under mild conditions via a radical intermediate, suitable for late-stage functionalization. Gram-scale experiment was successfully performed with low catalyst loading, yielding the target product excellently. Additionally, this transformation can be carried out under atmospheric pressure and provides alternative routes to drug precursors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Lebin Su, Shimin Xie, Jianyu Dong, Neng Pan, Shuang-Feng Yin, Yongbo Zhou
Summary: The cyclization-coupling reaction of 2-bromoaryl ketones and terminal alkynes is achieved for the first time by copper catalysis, producing polyfunctional naphthyl aryl ethers with broad substrate scope and good yields.
Article
Chemistry, Organic
Vijaykumar H. Thorat, Yu-Lin Tsai, Yong-Ran Huang, Chien-Hong Cheng, Jen-Chieh Hsieh
Summary: In this study, a nickel-catalyzed cyclization reaction was reported, which allowed the generation of polysubstituted biaryl sultams by reacting 1,2,3,4-benzothiatriazine-1,1-dioxides with arynes. The reaction exhibited high tolerance towards substituents on every subunit. Mechanistic investigation revealed the formation of a diradical intermediate, which reacted with a nickel complex to form a nickelacycle intermediate and underwent subsequent cyclization through aryne insertion.
Article
Chemistry, Organic
Qiong Liu, Zhaolong Ma, Jing Zhang, Xu-Qin Li
Summary: A rhodium-catalyzed method for synthesizing phenylacetate has been developed, which involves direct C-H carboxymethylation of anilines with removable directing groups. This reaction works most efficiently in air without the need for external bases or oxidants. The method provides a convenient and versatile access to various bioactive 2-amino aromatic acetic acid derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Min Zhang, Zhangyi Fu, Anping Luo, Xingwen Pu, Menglei Wang, Ying Huang, Yudong Yang, Jingsong You
Summary: The study presents a concise route for site-selective arylation of polycyclic aromatic hydrocarbons with easily available aryl sources, contributing to the bottom-up preparation of pi-extended PAHs. Additionally, a C8-H annulation protocol has been developed to rapidly assemble benzanthrones by simply switching the solvent to 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP).
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Stephane Golling, Pierre Hansjacob, Nassim Bami, Frederic R. Leroux, Morgan Donnard
Summary: This paper reports a palladium-catalyzed annulation reaction that can synthesize polysubstituted amino-indenones, with different regioselectivity observed between different ynamides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Huihong Wang, Fei Cao, Weiwei Gao, Xiaodong Wang, Yuhang Yang, Tao Shi, Zhen Wang
Summary: Epoxides have been utilized as alkylating reagents in Pd(II)-catalyzed C-H alkylation and oxidative annulation to synthesize isoquinolones instead of isochromans. By modifying the reaction mechanism with the addition of oxidant and TEA, various isoquinolones have been successfully prepared with high yields up to 92%. This methodology has also been applied in the total syntheses of rupreschstyril, siamine, and cassiarin A in an efficient manner.
Review
Chemistry, Applied
Xiao Yang, Rui Sun
Summary: Transition-metal-catalyzed oxidative annulation reactions are efficient methods for the synthesis of benzo-fused heterocyclic compounds. This review focuses on recent developments in reaction conditions and coupling reagents, aiming to provide sustainable and versatile strategies for the construction of heterocyclic skeletons found in drugs and bioactive molecules. The review summarizes and categorizes the annulation mechanisms with different coupling reagents.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Feihua Luo, Shuhua He, Quan Gou, Jinyang Chen, Mingzhong Zhang
Summary: This study investigated a simple Pd(OAc)(2) catalyzed ortho-hydroxylation of benzoic acids using TBHP as the sole oxidant. The protocol showed a relatively broad substrate scope and operational simplicity, with good compatibility with ortho-substituted substrates as an effective complement to previous ortho-hydroxylation reactions.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Siti Nur Fairuz Binte Sheikh Ismail, Binmiao Yang, Yu Zhao
Summary: In this study, a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones was successfully achieved, leading to the construction of a novel spirocyclic tetrahydroquinoline scaffold with high stereoselectivity.
Article
Chemistry, Organic
Qi Li, Zi-Lu Wang, Huan-Xuan Lu, Yun-He Xu
Summary: A copper-catalyzed 1,4-protosilylation of alpha-alkynyl-enones has been developed to prepare functionalized chiral homoallenylsilanes with a contiguous stereogenic center and axis, showing good yields and excellent enantioselectivities and diastereoselectivities.
Article
Chemistry, Multidisciplinary
Haibo Xu, Shengming Ma
Summary: An efficient method for synthesizing benzazocines through a double allene protocol has been developed. The reaction involves a highly selective palladium-catalyzed formal [6+2] annulation of allenyl benzoxazinanones with terminal allenes, resulting in the formation of challenging 8-membered cycles. The reaction exhibited decent yields, excellent regioselectivity, and remarkable Z-stereoselectivity for the exo-cyclic C=C bonds. The synthetic potential of benzazocine products has been demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Qiuling Song, Fumei Ke, Changjiang Yu, Xin Li, Heyun Sheng
Summary: A convenient method for synthesizing fluorine-containing heterocyclic compounds was developed, involving copper-catalyzed free radical addition and molecular lactone exchange of alkynol and ethyl bromodifluoroacetate. This method offers easy availability of raw materials, good stereochemical selectivity, and simple operation. It also allows for the synthesis of valuable tetrasubstituted E-configurated alkenes and various vinyl C-Br bonds and difluoromethylene-containing functionalized heterocycles.
Article
Chemistry, Organic
Jianxiao Li, Liying Cen, Dan He, Daohao Zhou, Songxuan Huang
Summary: A highly efficient palladium-catalyzed cascade desulfitative arylation of acetylinic oximes and sodium arylsulfinates with oxygen as the sole oxidant is described herein, providing access to structurally diverse 4-aryl isoxazoles. The catalytic system shows mild conditions, broad substrate scope, and operational simplicity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jeishla L. M. Matos, Suhelen Vasquez-Cespedes, Jieyu Gu, Takuya Oguma, Ryan A. Shenvi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
