Rh (III)-catalyzed C(sp2)-H functionalization/cyclization cascade of N-carboxamide indole and iodonium reagent for access to indoloquinazolinone derivatives

2021 ◽  
Author(s):  
Zhi-Peng Han ◽  
Mengmeng Xu ◽  
Rui-Ying Zhang ◽  
Xiao-Ping Xu ◽  
Shun-Jun Ji
Keyword(s):  
Functional Group ◽  
Mild Conditions

Rhodium-catalyzed synthesis of indoloquinazoline from readily available hypervalent iodonium reagent and N-carboxamide indole was developed. The protocol features broad functional group tolerance, mild conditions, excellent yields and simple workup. Notably,...

Asymmetric Synthesis of α-Alkylated γ-Lactam via Nickel/8-Quinim-Catalyzed Reductive Alkyl-Carbamoylation of Unactivated Alkene

Synlett ◽  
2021 ◽  
Author(s):  
Xianqing Wu ◽  
Mohini Shrestha ◽  
Yifeng Chen
Keyword(s):  
Functional Group ◽  
Enantioselective Synthesis ◽  
Chiral Auxiliary ◽  
Alkyl Iodide ◽  
General Strategy ◽  
Chemical Bonds ◽  
Mild Conditions ◽  
Chiral Carbon ◽  
Enantioselective Reaction ◽  
Metal Catalyzed

AbstractChiral-auxiliary-mediated synthesis represents the most frequently used synthetic tool for the induction of chirality on α-position of γ-lactams in organic synthesis. However, the general strategy requires the stoichiometric use of chiral reagents with multiple manipulation steps. Transition-metal-catalyzed asymmetric alkene dicarbofunctionalization using readily available substrates under mild conditions allows the simultaneous construction of two vicinal chemical bonds and a chiral carbon center, hence, gain expedient access to chiral heterocycles. Herein, we disclose a Ni-catalyzed enantioselective reaction of 3-butenyl carbamoyl chloride and primary alkyl iodide enabled by a newly designed chiral 8-quinoline imidazoline ligand (8-Quinim). This protocol features broad functional group tolerance and high enantioselectivities, achieving unprecedented synthesis of chiral nonaromatic heterocycles via catalytic reductive protocol.1 Introduction2 Development of 8-Quinim Ligand3 Nickel/8-Quinim-Catalyzed Enantioselective Synthesis of Chiral α-Alkylated γ-Lactam4 Conclusion and Outlook

scholarly journals Homocoupling of terminal alkynes catalyzed by CuCl under solvent-free conditions

2021 ◽  
pp. 174751982110325
Author(s):  
Yan Xiao ◽  
Jiyu Gao ◽  
Peng Chen ◽  
Guangliang Chen ◽  
Zicheng Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Reaction Times ◽  
Environmentally Friendly ◽  
Solvent Free ◽  
Copper Salt ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Solvent Free Conditions ◽  
Environmentally Friendly Process

A series of symmetrical 1,4-disubstituted buta-1,3-diynes is prepared with excellent yields (up to 95%) through homocoupling of terminal alkynes catalyzed by a copper salt under solvent-free conditions. This method provides an environmentally friendly process to prepare 1,3-diynes in short reaction times under mild conditions. Furthermore, the method is suitable for a wide substrate scope and has excellent functional group compatibility. The reaction can also be scaled up to gram level.

Direct and metal-free oxidative amination of sp3 C–H bonds for the construction of 2-hetarylquinazolin-4(3H)-ones

2016 ◽  
Vol 3 (9) ◽  
pp. 1096-1099 ◽  
Author(s):  
Huanhuan Liu ◽  
Tianran Zhai ◽  
Shiteng Ding ◽  
Yalei Hou ◽  
Xiangyu Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
New Method ◽  
Oxidative Amination ◽  
Metal Free ◽  
Mild Conditions

New method for synthesis of 2-hetarylquinazolin-4(3H)-ones from 2-aminobenzamides and (2-azaaryl)methanes under transition-metal free conditions, featuring a wide substrate scope with a broad range of functional group tolerance under mild conditions.

Bromotrifluoromethane: A Useful Reagent for Hydrotrifluoromethylation of Alkenes and Alkynes

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1028-1032 ◽  
Author(s):  
Xing Zheng ◽  
Xingang Zhang ◽  
Yu-Yan Ren
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Functional Group ◽  
Mild Conditions ◽  
Industrial Material ◽  
Reaction Proceeds

Bromotrifluoromethane (CF3Br) is a simple, inexpensive and abundant industrial material employed as a trifluoromethylating reagent. However, only limited strategies using CF3Br as a fluorine source are reported. Herein, we describe a visible-light-induced hydrotrifluoromethylation of alkenes and alkynes with CF3Br. The reaction proceeds under mild conditions with good functional group tolerance, providing a new route for the application of BrCF3 in organic synthesis.

Gold-catalyzed highly efficient benzylation of alcohols with N-Cbz-N-benzyl-propargylamine

2015 ◽  
Vol 2 (1) ◽  
pp. 34-37 ◽  
Author(s):  
Jing-Rui Zhao ◽  
Xiaolong Yuan ◽  
Zhaoyan Wang ◽  
Shiwu Chen ◽  
Zhan-Xin Zhang ◽  
...  
Keyword(s):  
Functional Group ◽  
Mild Conditions ◽  
Highly Efficient

Functional group tolerance under mild conditions eliminates the need for base additives or hygroscopic promoters.

Nickel-Catalyzed Reductive Monofluoroakylation of Alkyl Tosylate with Bromofluoromethane to Access Primary Alkyl Fluoride

2021 ◽  
Author(s):  
Ru Cui ◽  
Jie Sheng ◽  
Bing-Bing Wu ◽  
Duo-Duo Hu ◽  
Hong-Qian Zheng ◽  
...  
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Low Cost ◽  
Raw Material ◽  
Mild Conditions

A nickel-catalysed direct terminal monofluormethlyation between alkyl tosylates and a low-cost, industrial raw material bromofluoromethane has been developed. This transformation has demonstrated high efficiency, mild conditions, and good functional-group compatibility....

scholarly journals Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN2 pincer ligand

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingjie Zhang ◽  
Di Qi ◽  
Chenchen Jiao ◽  
Xiaopan Liu ◽  
Guisheng Zhang
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Materials Science ◽  
Alkylating Agents ◽  
Sonogashira Coupling ◽  
Pincer Ligand ◽  
One Pot ◽  
Mild Conditions ◽  
Alkyl Amines ◽  
Sonogashira Reactions

AbstractAlkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.

Electrophilic Amination with Anthranils through Thioamide-Assisted Cobalt(III)-Catalyzed C(sp3)–H Activation

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3881-3890
Author(s):  
Jie Li ◽  
Lei Liu ◽  
Zhao Zhang ◽  
Yucheng Wang ◽  
Yan Zhang
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Atom Economy ◽  
Electrophilic Amination ◽  
Amino Aldehydes ◽  
Mild Conditions ◽  
Weakly Coordinating

Cobalt(III)-catalyzed electrophilic amination of inert C(sp3)–H bonds of weakly coordinating thioamides with readily accessible anthranil derivatives was accomplished under mild conditions, with good functional group tolerance, thus providing various amino aldehydes and amino ketones. Moreover, our protocol with the versatile [Cp*Co(MeCN)3][SbF6]2 features excellent atom-economy and oxidant-free conditions, and allows facile late-stage functionalization.

Metal-free Reduction of Nitro Aromatics to Amines with B2(OH)4/H2O

Synlett ◽  
2018 ◽  
Vol 29 (13) ◽  
pp. 1765-1768 ◽  
Author(s):  
Haifeng Zhou ◽  
Yasuhiro Uozumi ◽  
Danyi Chen ◽  
Yanmei Zhou ◽  
Sensheng Liu ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Functional Group ◽  
Hydrogen Donor ◽  
Metal Free ◽  
Mild Conditions ◽  
Nitro Aromatics

A metal-free reduction of nitro aromatics mediated by di­boronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang
Keyword(s):  
Visible Light ◽  
Aromatic Compounds ◽  
Functional Group ◽  
Simple Procedure ◽  
One Pot ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Conventional Methods ◽  
Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

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