Article
Chemistry, Organic
Jiayuan Wang, Youwan Ye, Tongzhi Sang, Chenxing Zhou, Xiazhen Bao, Yong Yuan, Congde Huo
Summary: A general C(sp3)-H/C(sp3)-H dehydrogenative coupling strategy for the preparation of various natural or unnatural amino acids from readily available glycine derivatives and hydrocarbons is reported, which involves a combination of SET and HAT process.
Review
Chemistry, Multidisciplinary
Jianbin Li, Chia-Yu Huang, Chao-Jun Li
Summary: This review summarises recently developed strategies for achieving C-C cross-couplings between an inert aliphatic C-H bond and another C-H bond through different C(sp3)-H functionalisation tactics.
TRENDS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Fang Wang, Qianting Zhou, Xinying Zhang, Xuesen Fan
Summary: A novel and efficient alpha-C(sp(3))-H alkenylation of cyclic amines with maleimides was presented, featuring readily available and structurally diverse substrates, a green and economical catalyst, a unique reaction pathway, mild reaction conditions, high efficiency, and excellent atom economy. This new reaction enriches the application of Fe(III)-catalyzed C(sp(3))-H activation and functionalization.
JOURNAL OF ORGANIC CHEMISTRY
(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
Cui-Lian Zeng, Hao Wang, Di Gao, Zhen Zhang, Dong Ji, Wei He, Cheng-Kou Liu, Zhao Yang, Zheng Fang, Kai Guo
Summary: This study presents a green and gentle Minisci-type reaction method, in which the cross-dehydrogenative coupling of heteroarenes with aliphatic C(sp(3))-H bonds is achieved under visible-light irradiation. This method does not require oxidants or transition metal catalysts, and only the catalytic equivalent of CF3SO2Na and room temperature are needed to ensure an efficient reaction.
Article
Chemistry, Organic
Hong-Yu Zhang, Jianjun Chen, Cong-Cong Lu, Ya-Ping Han, Yuecheng Zhang, Jiquan Zhao
Summary: This study describes a cross-dehydrogenative-coupling reaction using visible light and air at room temperature to synthesize aminomethyl-substituted N-heterocycles, providing an efficient, environmentally friendly, and convenient method.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yi-Fan Zhang, Han-Nan Chen, Yi Xiao, Zhencun Cui, Wei David Wang, Guo-Qiang Xu
Summary: Here, a novel protocol for synthesizing alpha-functionalized saturated aza-heterocycles is presented, allowing for the easy installation of various nucleophilic groups. Additionally, a range of biologically valuable 3,3'-diindolylmethane derivatives can be readily synthesized under mild photocatalytic conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fufang Wu, Xuanzhen Han, Xuejian Li, Xiaobao Shen, Chang Wang, Zhimei Tian, Bin Cheng, Jingbin Zhang, Liangquan Sheng, Hongbin Zhai
Summary: The paper describes a method for the selective C-H functionalization of alkanes using iodine(III) as a mediator. The radical coupling of N-hydroxyphthalimide with unactivated alkanes is achieved, providing a way to construct new chemical bonds under mild reaction conditions. The method allows for efficient functionalization of unactivated hydrocarbons with good yields.
COMMUNICATIONS CHEMISTRY
(2021)
Article
Chemistry, Organic
Xinpeng Xie, Kaikai Qiao, Bing-ru Shao, Wenfeng Jiang, Lei Shi
Summary: Cross-dehydrogenative coupling is a powerful tool for constructing C-C and C-heteroatom bonds. In this study, a visible-light-mediated radical CDC of C(sp(3))-H/C(sp(3))-H and C(sp(3))-H/C(sp(2))-H was reported, guided by a phenyl radical and intermolecular hydrogen atom transfer process. This strategy enables the efficient coupling of inert C(sp(3))-H and C(sp(2))-H with alpha-N C(sp(3))-H of amines, showing good regioselectivities and yields. Mechanistic studies revealed that the EDA complex triggers an intermolecular HAT process.
Article
Chemistry, Organic
Zhengbao Xu, Yameng Gao, Shanshan Wang, Qili Zhang, Lizhi Zhang, Liang Shen
Summary: An efficient free-radical-promoted unactivated C(sp(3))-H dehydrogenative coupling reaction of free alcohols at the delta position with quinone and chromone has been developed. This reaction shows good functional group tolerance and substrate scope, providing moderate to good yields of C(sp(2))-H alkylation products. It is a sustainable and practical strategy for the late-stage functionalization of alcohols with quinones and chromones by constructing challenging C(sp(3))-C(sp(2)) bonds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Yujun Li, Shaopeng Guo, Qing-Han Li, Ke Zheng
Summary: This paper presents a mild, metal-free method for constructing alpha-tertiary amino acids (ATAAs) using the cross-dehydrogenative coupling (CDC) reaction. The method exhibits excellent functional group tolerance and late-stage applicability, and allows for the synthesis of ATAAs under mild conditions.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Jin-Yu He, Wei-Feng Qian, Yan-Zhao Wang, Chaochao Yao, Nana Wang, Huilin Liu, Bing Zhong, Cuiju Zhu, Hao Xu
Summary: A novel catalyst-free, direct electrooxidative method has been developed for the mono- and di-alkylation of phenol derivatives at C(sp(3))-H. This approach allows for selective alkylations under mild conditions without the need for metals or external oxidants, using readily available electrodes. The study demonstrates a broad substrate scope and excellent selectivity for C-C, C-N, C-O bond formation, with the potential for further late-stage diversification.
Article
Chemistry, Organic
Ravichandran Logeswaran, Masilamani Jeganmohan
Summary: This paper reports an oxidative cross-coupling reaction between α,β-unsaturated compounds and unactivated alkenes via cobalt-catalyzed vinylic C-H activation. The reaction was investigated with differently functionalized unsaturated compounds and unactivated olefins, leading to the preparation of valuable amide functionalized butadienes and indenones in good yields. A possible reaction mechanism involving directed olefinic C-H activation through a base-assisted deprotonation pathway is proposed.
Article
Chemistry, Multidisciplinary
Ruocheng Sang, Wangyujing Han, Hanwen Zhang, Carla M. Saunders, Adam Noble, Varinder K. Aggarwal
Summary: Copper catalysts can promote the dehydrogenative borylation of alkanes with bis(catecholato)diboron under oxidant-free conditions. This is due to the unexpected dual role of the copper catalyst, which promotes the oxidation of the diboron reagent and generates an electrophilic bis-boryloxide that acts as an effective borylating agent in subsequent redox-neutral photocatalytic C-H borylations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Multidisciplinary
Stavros K. Kariofillis, Abigail G. Doyle
Summary: In recent years, the development of light-driven reactions has made significant advancements in synthetic organic chemistry, particularly in combining photoredox and nickel catalysis for challenging cross-coupling reactions. The question of whether photo-induced activation of the nickel catalyst itself could lead to new approaches to cross-coupling has been explored. By utilizing a visible-light-driven mechanism for chlorine radical formation and conducting mechanistic investigations on organometallic Ni complexes relevant to cross-coupling, the study aims to facilitate new catalyst design and develop novel synthetic methods.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Hariprasad Aruri, Umed Singh, Sumit Sharma, Satish Gudup, Mukesh Bhogal, Sanjay Kumar, Deepika Singh, Vivek K. Gupta, Rajni Kant, Ram A. Vishwakarma, Parvinder Pal Singh
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Hariprasad Aruri, Umed Singh, Sanjay Kumar, Manoj Kushwaha, Ajai Prakash Gupta, Ram A. Vishwakarma, Parvinder Pal Singh
Article
Chemistry, Medicinal
Umed Singh, Gousia Chashoo, Sameer U. Khan, Priya Mahajan, Amit Nargotra, Girish Mahajan, Amarinder Singh, Anjna Sharma, Mubashir J. Mintoo, Santosh Kumar Guru, Hariprasad Aruri, Thanusha Thatikonda, Promod Sahu, Pankaj Chibber, Vikas Kumar, Sameer A. Mir, Sonali S. Bharate, Sreedhar Madishetti, Utpal Nandi, Gurdarshan Singh, Dilip Manikrao Mondhe, Shashi Bhushan, Fayaz Malik, Serge Mignani, Ram A. Vishwakarma, Parvinder Pal Singh
JOURNAL OF MEDICINAL CHEMISTRY
(2017)
Article
Oncology
Sameer Ullah Khan, Kaneez Fatima, Umed Singh, Parvinder Paul Singh, Fayaz Malik
Summary: Metastasis is a major challenge in cancer biology and can lead to patient death. The cell cycle regulation and stress response of circulating tumor cells (CTCs) are crucial for their survival and progression, making them a potential target for metastatic disease treatment. A novel CDK inhibitor, 4ab, induces autophagy and endoplasmic reticulum stress in aggressive cancer cells, resulting in paraptosis. It effectively induces cell death through ER stress-mediated activation of JNK signaling and reduces tumor burden and micro-metastasis in tumor-bearing mice.