Article
Chemistry, Organic
Caijin Zeng, Songjia Fang, Shuqi Guo, Huanfeng Jiang, Shaorong Yang, Wanqing Wu
Summary: A novel and efficient palladium-catalyzed annulation of anilines with bromoalkynes for the synthesis of 2-phenylindoles has been described. This approach features excellent regio- and stereoselectivities and good functional group tolerance. Preliminary mechanistic studies indicate that anilines undergo anti-nucleophilic addition to bromoalkynes to generate (Z)-N-(2-bromo-1-phenyl-vinyl) anilines, followed by sequential C-H functionalization to deliver different substituted 2-phenylindoles. This method provides potential applications for the construction of various biologically active compounds.
Article
Chemistry, Organic
Yue-Xiao Wu, Ming-Hui Huang, Kang Peng, Zhen Shi, Er-jun Hao, Zhi-Bing Dong
Summary: An iodine-catalyzed one-pot synthesis of benzoazole-substituted thioenamines was reported. The reaction proceeds through an electrophilic substitution pathway in a cross dehydrogenation coupling manner. The protocol is metal-free, easy to perform, tolerates various functional groups, and provides good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Teng-Fei Zhao, Xiao-Li Xu, Wei-Yin Sun, Yi Lu
Summary: In this study, we report a strategy for Rh(III)-catalyzed direct ortho-C-H bond carbonylation to construct benzoxazinones from anilines and their derivatives with high atom economy. Interestingly, in situ generation of corresponding amides from anilines occurred when excess Ac2O was added and directed the following C-H bond carbonylation to form benzoxazinones. The method allows extensive functional group tolerance when alkyl amide directing groups are installed. Additionally, it shows potential application in the convenient derivatization of drugs with aryl amine groups.
Article
Chemistry, Organic
Nuan Chen, Ting Zhou, Hong Zhang, Yuqi Zhu, Ming Lang, Jian Wang, Shiyong Peng
Summary: An unprecedented copper-catalyzed tandem reaction of 1,6-enynes with diazo compounds via a cross-coupling/[2 + 2] cycloaddition sequence was reported, leading to the synthesis of a library of methylenecyclobutane-fused ring systems with high proximal-regioselectivity and diastereoselectivity. Moreover, the key intermediate of 1,6-allenene proceeds via a thermally promoted [2 + 2] cycloaddition in the absence of copper catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaogang Yang, Dong Lu, Wenjian Guan, Shuang-Feng Yin, Nobuaki Kambe, Renhua Qiu
Summary: R2PCF2H ligands and their precursors were synthesized by adjusting water concentration. These ligands can be stabilized in Cu(I) clusters and enable fast Sonogashira cross-coupling reaction at room temperature.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Jingyu Zhang, Wei Xia, Saskia Huda, Jas S. Ward, Kari Rissanen, Markus Albrecht
Summary: A copper(II)-catalyzed dearomative cyclization amination of N-(2-aminobenzoyl) indoles is described, yielding tetracyclic indolines under mild conditions with good yields. Tetracyclic 5a,6-dihydroindolo[2,1-b]quinazolin-12(5H)-ones are obtained in good to excellent yields (up to 99% yield) by N-Ts bond cleavage using trifluoromethanesulfonic acid (TfOH) mediation. The resulting compounds can be easily functionalized through simple synthetic methods.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Canlin Zou, Hongting Wu, Jiangtao He, Yunfei Hu, Weijie Deng, Xinling Li, Jinhui Hu, Yibiao Li, Yubing Huang
Summary: An efficient anodic C(sp(3))-H acyloxylation protocol has been developed, which enables the direct oxidation of indolin-3-ones to obtain various C2-acyloxy indolin-3-ones without the need for metal catalysts and external oxidants. The practicality of this protocol has been demonstrated through the effective application of several medical drugs and gram-scale experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dmitry A. A. Dulov, Tatiana V. V. Magdesieva
Summary: It has been demonstrated that inexpensive and readily available N,N'-diaryldihydrophenazines can effectively replace Ir(III)- and Ru(II)-based photocatalysts in the dual photoredox/Ni(II)C-N coupling of aryl halides with a wide range of anilines, as shown by 32 examples. This efficient and operationally simple approach to diarylamines can be scaled up using a flow apparatus.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Benxiang Zhang, Jiayan He, Yang Gao, Laura Levy, Martins S. Oderinde, Maximilian D. Palkowitz, T. G. Murali Dhar, Michael D. Mandler, Michael R. Collins, Daniel C. Schmitt, Philippe N. Bolduc, Teyu Chen, Sebastian Clementson, Nadia Nasser Petersen, Gabriele Laudadio, Cheng Bi, Yu Kawamata, Phil S. Baran
Summary: Modern retrosynthetic analysis in organic chemistry is a method that guides the design of synthetic routes based on the polar relationships between functional groups. This approach assigns charges to functional groups and disconnects bonds between them. It has applications in undergraduate curriculum and synthetic methods, but requires careful considerations to overcome selectivity and oxidation state issues. In this study, a radical-based Ni/Ag-electrocatalytic cross-coupling of substituted carboxylic acids was reported, enabling a simplified approach to accessing complex molecular architectures.
Article
Chemistry, Organic
Guan-Jun Wang, Le Wang, Guo-Dong Zhu, Jia Zhou, He-Yuan Bai, Shu-Yu Zhang
Summary: This study describes an efficient method for the synthesis of chiral tetrahydroindole pyrazolinones through chiral phosphoric acid-catalyzed [3 + 2] cascade cyclizations, which exhibit a broad substrate scope, high yields, and excellent enantioselectivities. The research highlights the potential value of direct chiral indolizations from simple amine sources in organic synthesis.
Article
Chemistry, Organic
Kuei-Wei Chiu, Yu-Hsun Tseng, Ying-Xin Li, Rong-Jie Chein
Summary: In this study, a novel biomimetic synthesis of clavicipitic acid diastereomers was reported, utilizing a DDQ-mediated crossdehydrogenative coupling (CDC) reaction. The synthesis involved Suzuki coupling for prenylation and an intramolecular CDC reaction for the construction of the azepinoindole core. The trans isomer was obtained as the major product, and the two diastereomers were separable. The CDC reaction conditions were investigated, and a plausible mechanism for diastereoselectivity was proposed.
Article
Chemistry, Multidisciplinary
Yifan Wang, Yuanyuan Ping, Wangqing Kong
Summary: A cooperative Pd/Cu-catalyzed three-component cross-coupling reaction of alkynes, B 2 Pin 2 and alkenetethered aryl halides is reported. This reaction proceeds under mild conditions and shows broad substrate scope, providing a variety of heterocycles containing tetrasubstituted alkenylboronate moieties in synthetically useful yields with excellent chemoselectivity and regioselectivity. An enantioselective cascade cyclization/cross-coupling process has also been developed for the synthesis of enantiomerically enriched oxindole bearing a tetrasubstituted alkenylboronate moiety.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Guifang Chen, Bo Xu
Summary: An efficient method for constructing 3-sulfonylindoles and 2-methyleneindophenols via decarboxylative propargylation/hydroamination has been developed, using sodium sulfonates and phenols as the nucleophiles. The reaction features mild conditions, high chemoselectivity, and can be extended to other nucleophiles such as malonates, alcohols, and indoles. The broad substrate scope and scalability of this protocol make it practical for the synthesis of indole derivatives.
Article
Chemistry, Multidisciplinary
Quan-Bing Wang, Shi Tang, Ying-Jie Wang, Yue Yuan, Tieqiao Chen, Ai-Qun Jia
Summary: The PIDA mediated intramolecular oxidative C-N coupling and subsequent detosylative aromatization allowed for the synthesis of valuable indolo[2,3-b]quinoline derivatives, providing an efficient method for their preparation.
Article
Chemistry, Organic
Piao Lu, Weihui Zhuang, Leipeng Lu, Anyi Liu, Yixi Chen, Chenmeng Wu, Xiaofeng Zhang, Qiufeng Huang
Summary: Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials has been achieved. Mn(OAc)3.2H2O selectively promotes different reactions leading to the formation of two distinct products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)