scholarly journals The Use of Polymer Supports in Organic Synthesis. The Synthesis of Monotrityl Ethers of Symmetrical Diols

1972 ◽  
Vol 50 (17) ◽  
pp. 2892-2893 ◽  
Author(s):  
Clifford C. Leznoff ◽  
Jack Y. Wong
Keyword(s):  
Organic Synthesis ◽  
Acid Chloride ◽  
Functional Group ◽  
Selective Synthesis ◽  
Polymer Supports ◽  
Unique Method

A modified Merrifield polymer containing acid chloride groups was used in the selective synthesis of the monotrityl ethers of the symmetrical diols, HO—(CH2)n—OH, where n = 2, 4, 6, 8, and 10. This procedure constitutes a unique method of blocking one functional group of a completely symmetrical difunctional compound.

scholarly journals The Use of Polymer Supports in Organic Synthesis. II. The Syntheses of Monoethers of Symmetrical Diols

1973 ◽  
Vol 51 (15) ◽  
pp. 2452-2456 ◽  
Author(s):  
Jack Y. Wong ◽  
Clifford C. Leznoff
Keyword(s):  
Organic Synthesis ◽  
Support System ◽  
Functional Group ◽  
Polymer Support ◽  
Reaction Conditions ◽  
Polymer Supports ◽  
Unique Method ◽  
Insoluble Polymer

An insoluble polymer support system was used as a unique method of blocking one functional group of a completely symmetrical difunctional compound. The monotetrahydropyranyl and monotrityl ethers of the symmetrical diols, HO—(CH2)n—OH, where n = 2,4,6,8, and 10, were prepared. Reaction conditions for the preparation of the monotetrahydropyranyl ether of 1,10-decanediol were optimized.

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.

Ligand-Driven Advances in Iridium Catalyzed sp3 C-H Borylation: 2,2’-Dipyridylarylmethane

Synlett ◽  
2020 ◽  
Author(s):  
Margaret R Jones ◽  
Nathan D. Schley
Keyword(s):  
Recent Work ◽  
Organic Synthesis ◽  
Functional Group ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Additional Ligand ◽  
Limited Application ◽  
Hydrocarbon Substrates ◽  
Phenanthroline Ligands

The field of catalytic C-H borylation has grown considerably since its founding, providing a means for the preparation of synthetically versatile organoborane products. While sp2 C-H borylation methods have found widespread and practical use in organic synthesis, the analogous sp3 C-H borylation reaction remains challenging and has seen limited application. Existing catalysts are often hindered by incomplete consumption of the diboron reagent, poor functional group tolerance, harsh reaction conditions, and the need for excess or neat substrate. These challenges acutely affect C-H borylation chemistry of unactivated hydrocarbon substrates, which has lagged in comparison to methods for the C-H borylation of activated compounds. Herein we discuss recent advances in sp3 C-H borylation of undirected substrates in the context of two particular challenges: (1) utilization of the diboron reagent and (2) the need for excess or neat substrate. Our recent work on the application of dipyridylarylmethane ligands in sp3 C-H borylation has allowed us to make contributions in this space and has presented an additional ligand scaffold to supplement traditional phenanthroline ligands.

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.

Soluble polymer-supported organocatalysts

2012 ◽  
Vol 85 (3) ◽  
pp. 493-509 ◽  
Author(s):  
Yun-Chin Yang ◽  
David E. Bergbreiter
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Soluble Polymer ◽  
Soluble Polymers ◽  
The Past ◽  
Polymer Supports ◽  
Polymer Supported ◽  
Simple Product

Organocatalysts have been extensively studied for the past few decades as alternatives to transition-metal catalysts. Immobilizing organocatalysts on polymer supports allows easy recovery and simple product purification after a reaction. Select examples of recent reports that describe the potential advantages of using soluble polymers to prepare soluble polymer-supported organocatalysts useful in organic synthesis are reviewed.

scholarly journals Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents

Molecules ◽  
2020 ◽  
Vol 25 (1) ◽  
pp. 230 ◽  
Author(s):  
Elwira Bisz ◽  
Michal Szostak
Keyword(s):  
Organic Synthesis ◽  
Nucleophilic Addition ◽  
Functional Group ◽  
High Selectivity ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Grignard Reagents ◽  
High Importance ◽  
Iron Salts ◽  
The Cross

Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.

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