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.

scholarly journals Cu/Pd-catalyzed borocarbonylative trifunctionalization of alkynes and allenes: synthesis of β-geminal-diboryl ketones

2021 ◽  
Author(s):  
Yang Yuan ◽  
Fu-Peng Wu ◽  
Anke Spannenberg ◽  
Xiao-Feng Wu
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Building Blocks ◽  
Mechanistic Studies ◽  
Efficient Strategy ◽  
New Class ◽  
Reaction Proceeds

AbstractFunctionalized bisboryl compounds have recently emerged as a new class of synthetically useful building blocks in organic synthesis. Herein, we report an efficient strategy to synthesize β-geminal-diboryl ketones enabled by a Cu/Pd-catalyzed borocarbonylative trifunctionalization of readily available alkynes and allenes. This reaction promises to be a useful method for the synthesis of functionalized β-geminal-diboryl ketones with broad functional group tolerance. Mechanistic studies suggest that the reaction proceeds through borocarbonylation/hydroboration cascade of both alkynes and allenes.

Synthesis of Isoquinoline-1,3(2H,4H)-diones by Visible-light-mediated the Cyclization of Acryloylbenzamides with Alkyl Boronic Acids, Arylsulfonylhydrazides and Oxime Esters

Synthesis ◽  
2022 ◽  
Author(s):  
Jiahui Fu ◽  
Xingxing Cai ◽  
Yihuo Liu ◽  
Jing-Hua Li ◽  
Dongping Cheng ◽  
...  
Keyword(s):  
Visible Light ◽  
Bioactive Compounds ◽  
Boronic Acids ◽  
Radical Addition ◽  
Tandem Reaction ◽  
Good Opportunity ◽  
Mild Conditions ◽  
Reaction Proceeds

An efficient visible-light-mediated tandem reaction of acryloylbenzamides with alkyl boronic acids, arylsulfonylhydrazides and oxime esters is developed. The reaction proceeds the radical addition and cyclization to give various isoquinoline-1,3(2H,4H)-diones in satisfactory yields under mild conditions, which provides a good opportunity to discover new meaningful bioactive compounds.

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.

A mild, general, and metal-free method for site-specific deuteration induced by visible light using D2O as the source of deuterium atoms

2020 ◽  
Vol 22 (3) ◽  
pp. 669-672 ◽  
Author(s):  
Shuai Shi ◽  
Ruining Li ◽  
Liangming Rao ◽  
Zhankui Sun
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Site Specific ◽  
Metal Free ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Radical Approach

Visible light induced desulfurization–deuteration method was developed using D2O as the source of deuterium atoms. This radical approach features mild conditions, broad substrate scope, highly efficient D-incorporation and excellent functional group compatibility.

Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Devaiah Vytla ◽  
Kumargurubaran Kaliyaperumal ◽  
Rajeswari Velayuthaperumal ◽  
Parinita Shaw ◽  
Raj Gautam ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Cyclization ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Reaction Proceeds ◽  
High Yields

AbstractA photocatalyzed and highly efficient trifluoromethylation of N-arylvinylsulfonamides using commercially available CF3SO2Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in good to excellent yields.

scholarly journals One-Pot Reductive Acetylation of Aldehydes using 1-Hydrosilatrane in Acetic Acid

SynOpen ◽  
2019 ◽  
Vol 03 (01) ◽  
pp. 1-3 ◽  
Author(s):  
Reuben James ◽  
Sharon Herlugson ◽  
Sami Varjosaari ◽  
Vladislav Skrypai ◽  
Zainab Shakeel ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Organic Synthesis ◽  
Functional Group ◽  
Building Blocks ◽  
Flash Chromatography ◽  
Primary Alcohols ◽  
Facile Synthesis ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Mild Conditions

A one-pot, direct reductive acetylation of aldehydes was achieved under mild conditions using 1-hydrosilatrane as a safe and easily accessible catalyst. Described herein is a facile synthesis that produces acylated primary alcohols that can serve as valuable building blocks for organic synthesis. The method has good functional group tolerance and works for a range of aryl aldehydes, with the notable exception of electron-rich arenes. A library of esters was isolated by flash chromatography in yields as high as 92%.

scholarly journals A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C–H Alkylation of Alcohols

Synthesis ◽  
2020 ◽  
Vol 52 (15) ◽  
pp. 2171-2189
Author(s):  
Kounosuke Oisaki ◽  
Motomu Kanai ◽  
Kentaro Sakai
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Organic Synthesis ◽  
Hydroxy Group ◽  
Functional Group ◽  
Chemical Yield ◽  
Catalyst System ◽  
Hydrogen Atom Transfer ◽  
Hybrid Catalyst ◽  
Site Selective

The development of catalyst-controlled, site-selective C(sp3)–H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid–ethanolamine complex enhances the chemical yield of the α-C–H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched­ peptides.

scholarly journals Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5532
Author(s):  
Laëtitia Chausset-Boissarie ◽  
Nicolas Cheval ◽  
Christian Rolando
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Materials Science ◽  
Cross Coupling ◽  
High Yield ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Novel Strategy

Monofluoroalkenes are versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with primary and strained secondary alkylboronic acids under mild conditions. This novel strategy gives access to a wide range of functionalized tri- and tetrasubstituted monofluoroalkenes in high yield, with good functional group tolerance, independently from the gem-bromofluoroalkenes geometry.

scholarly journals Dual Ni/photoredox-catalyzed asymmetric cross-coupling to access chiral benzylic boronic esters

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Purui Zheng ◽  
Pan Zhou ◽  
Dong Wang ◽  
Wenhao Xu ◽  
Hepan Wang ◽  
...  
Keyword(s):  
Visible Light ◽  
Ambient Temperature ◽  
Functional Group ◽  
Cross Coupling ◽  
Strong Base ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Boronic Esters

AbstractThe flourishing Ni/photoredox-catalyzed asymmetric couplings typically rely on redox-neutral reactions. In this work, we report a reductive cross-coupling of aryl iodides and α-chloroboranes under a dual catalytic regime to further enrich the metallaphotoredox chemistry. This approach proceeds under mild conditions (visible light, ambient temperature, no strong base) to access the versatile benzylic boronic esters with good functional group tolerance and excellent enantioselectivities.

Lewis Acid-Mediated Efficient Synthesis of 4H-1,3-benzo-xazines and Their Derivatives 4,5-dihydro-1,3-benzo-xazepines

2020 ◽  
Vol 24 (11) ◽  
pp. 1263-1273
Author(s):  
An Junkai ◽  
Liu Jikun ◽  
Shi Ying ◽  
Zhu Weiwei ◽  
Guo Guoying ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Lewis Acid ◽  
Functional Group ◽  
Materials Science ◽  
Pharmaceutical Research ◽  
Direct Access ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Promising Strategy ◽  
Characteristic Features

: Compounds containing 4H-1,3-benzo-xazine core usually possess characteristic features and have been applied in the fields of organic synthesis, pharmaceutical research, materials science and bioscience. Here we reported convenient and direct access to 4H-1,3- benzo-xazines and their derivatives through intramolecular cyclization of olefinic amides or ureas with good to excellent yields in the presence of TMSOTf. The properties (mild conditions, metal or additives-free, wide substrate scope and functional group tolerance) of the process made it a promising strategy to synthesize various benzo-xazines and their derivatives.

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