Copper/Di-tert-butyl Peroxide-Catalyzed Regioselective Hydroxyphosphorylation of 1,3-Enynes

Synthesis ◽  
2021 ◽  
Author(s):  
Shaoqun Zhu ◽  
Jiawei Wang ◽  
Bing Zhou ◽  
Hong Hou
Keyword(s):  
Functional Group ◽  
Catalytic Amount ◽  
Radical Reactions ◽  
Reaction Conditions ◽  
Radical Initiator ◽  
Tert Butyl ◽  
Butyl Peroxide

AbstractThe copper/di-tert-butyl peroxide-catalyzed regioselective hydroxyphosphorylation of 1,3-enynes is described. The advantages of the reported radical reactions are excellent functional group tolerance, the use of a catalytic amount of copper and di-tert-butyl peroxide ( t BuOO t Bu) as a radical initiator, and mild reaction conditions. The desired products are obtained in moderate to excellent yields after purification.

Copper/tBuOOtBu-Catalyzed Regioselective Hydroxylphosphorylation of 1,3-Enynes

Synthesis ◽  
2021 ◽  
Author(s):  
Shaoqun Zhu ◽  
Jiawei Wang ◽  
Bing Zhou ◽  
Hong Hou
Keyword(s):  
Functional Group ◽  
Catalytic Amount ◽  
Radical Reactions ◽  
Reaction Conditions ◽  
Radical Initiator

A copper/tBuOOtBu-catalyzed regioselective hydroxyphosphorylation of 1,3-enynes is described. The present radical reactions have great functional group tolerance, catalytic amount of copper and tBuOOtBu as the radical initiator, mild reaction conditions and moderate to good isolated yields.

Copper-Catalyzed Oxidative Dimerization of 2-Oxindoles under Base-Free Conditions

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1485-1490 ◽  
Author(s):  
Wen-Ting Wei ◽  
Yi-Ling Huang ◽  
Wen-Hui Bao ◽  
Wei-Wei Ying ◽  
Wei-Ting Chen ◽  
...  
Keyword(s):  
Bond Formation ◽  
Radical Mechanism ◽  
Oxidative Dimerization ◽  
Radical Initiator ◽  
Tert Butyl ◽  
Simple Strategy ◽  
Efficient Route ◽  
Butyl Peroxide

A practical copper-catalyzed oxidative dimerization of 2-oxindoles using di-tert-butyl peroxide as the radical initiator under base-free conditions was achieved, which not only provided an efficient route to prepare various 3,3′-bioxindoles, but also represented a simple strategy for C(sp3)–H functionalization/C–C bond formation. A radical mechanism was proposed based on the reaction results and controlling experiments.

SN2’ Defluorinative Allylation of Trifluoromethylalkenes with Allylsilanes

Synthesis ◽  
2021 ◽  
Author(s):  
Meng-Meng Sun ◽  
Haidong Liu ◽  
Chuan Zhu ◽  
Chao Feng
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Catalytic Amount ◽  
Synthetic Chemistry ◽  
Potential Utility ◽  
Reaction Conditions

An SN2’ defluorinative allylation of trifluoromethylalkenes with readily available allylsilanes to access homoallyl gem-difluoroalkenes was reported. The reaction is triggered by catalytic amount of TBAF with the extruded fluoride in reaction serving as the sustainable activator for organosilanes. The high efficiency, good functional group tolerance, and mild reaction conditions enable the potential utility of this method in synthetic chemistry.

Iron-Catalyzed Carboiodination of Alkynes

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2974-2980 ◽  
Author(s):  
You-Gui Li ◽  
Hongli Bao ◽  
Weili Deng ◽  
Yajun Li
Keyword(s):  
Room Temperature ◽  
Cyano Group ◽  
Alkyl Chains ◽  
Radical Initiator ◽  
Tert Butyl ◽  
Butyl Peroxide ◽  
Alkyl Iodides ◽  
Vinyl Iodides ◽  
Fluoroalkyl Group

An iron-catalyzed carboiodination of alkynes with alkyl iodides­ at room temperature was developed. This method could provide synthetically useful vinyl iodides with general alkyl chains, fluoroalkyl group, ester, and cyano group. Conjugated alkynes or unconjugated alkynes were both suitable for this transformation. A radical pathway was proposed for the mechanism and acetyl tert-butyl peroxide was selected as the radical initiator. Alkenes could also be applied to this chemistry and produce more complex alkyl iodides.

Fundamental Thermal Hazard Investigation for Tert-Butyl Peroxide Reactor Using DSC and TGA Techniques

2011 ◽  
Vol 21 (1) ◽  
pp. 53-63 ◽  
Author(s):  
Chien-Jung Chen ◽  
Jen-Hao Chi ◽  
Sheng-Hung Wu ◽  
Cheng-Tung Chen ◽  
Hsiu-Fen Tsai
Keyword(s):  
Thermal Hazard ◽  
Tert Butyl ◽  
Butyl Peroxide

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3466-3472
Author(s):  
Yunkui Liu ◽  
Bingwei Zhou ◽  
Qiao Li ◽  
Hongwei Jin
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Previous Literature ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Multicomponent Coupling ◽  
Easy Operation

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Hongji Li ◽  
Wenjie Zhang ◽  
Xueyan Liu ◽  
Zhenfeng Tian
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Reaction Conditions ◽  
Bond Functionalization ◽  
Alkylation Process ◽  
Coupling Partner

AbstractWe herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

Sulfonyl Radical Triggered Selective Iodosulfonylation and Bicycli-zations of 1,6-Dienes

2021 ◽  
Author(s):  
Shi-Ping Wu ◽  
Dong-Kai Wang ◽  
Qing-Qing Kang ◽  
Guo-Ping Ge ◽  
Hongxing Zheng ◽  
...  
Keyword(s):  
Functional Group ◽  
High Selectivity ◽  
Reaction Conditions ◽  
First Time

A novel sulfonyl radical triggered selective iodosulfonylation and bicyclizations of 1,6-dienes has been described for the first time. High selectivity and efficiency, mild reaction conditions, excellent functional group compatibility, and...

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