Papers

With Tag: General Organic Chemistry

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TRAM Linker:  A Safety-Catch Linker for the Traceless Release of Acrylamides

Christopher J. Ciolli, Sean Kalagher, Peter J. Belshaw
Org. Lett. | 2004 | 10.1021/ol049711i

A novel safety-catch linker for the solid-phase synthesis of small-molecule libraries containing electrophilic reactive groups has been developed. Upon cleavage from solid support, the linker generates a Michael acceptor (an acrylamide) on each library...

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Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction

Steven P. Miller, James P. Morken, Jeremy B. Morgan
Org. Lett. | 2003 | 10.1021/ol036219a

Chiral nonsymmetric 1,2-diboron adducts are generated by catalytic enantioselective diboration. Oxidation of these adducts provides 1,2-diols in good yield. Alternatively, 1,2-diboron compounds may be reacted, in situ, with aryl halides wherein the less...

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A Simple Approach To Separate a Mixture of Homopropargylic and Allenic Alcohols

Fan Fu, Kim Le Mai Hoang, Teck-Peng Loh
Org. Lett. | 2008 | 10.1021/ol801087s

A simple and practical approach to separate homopropargylic alcohol from allenic alcohol has been developed. It involves the formation of an insoluble silver acetylide species between silver nitrate and homopropargylic alcohol in aqueous acetone which can be...

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Oxidative Cleavage of Alkenes Using an In Situ Generated Iodonium Ion with Oxone as a Terminal Oxidant

Prem P. Thottumkara, Thottumkara K. Vinod
Org. Lett. | 2010 | 10.1021/ol1023807

A facile and operationally convenient catalytic procedure for oxidative cleavage of alkenes is described. In situ formed [hydroxy(4-carboxyphenyl)iodonium]ion, 2, from the oxidation of 4-iodobenzoic acid, 1, has been shown to facilitate the cleavage of a...

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Chemoselective Chemical and Electrochemical Deprotections of Aromatic Esters

Kevin Lam, István E. Markó
Org. Lett. | 2009 | 10.1021/ol900828x

Alcohols can be easily and chemoselectively deprotected from the corresponding aromatic esters by using either SmI 2 /HMPA or by electrolysis in the presence of a proton source.

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Palladium-Catalyzed Decarboxylative Rearrangements of Allyl 2,2,2-Trifluoroethyl Malonates: Direct Access to Homoallylic Esters

Marvin J. Miller, Jerod Patzner, Lawrence P. Tardibono, Cara Cesario
Org. Lett. | 2009 | 10.1021/ol901518g

Homoallylic esters are obtained in a single transformation from allyl 2,2,2-trifluoroethyl malonates by using a Pd(0) catalyst. Facile decarboxylation of allyl 2,2,2-trifluoroethyl malonates is attributed to a decrease in pK a compared to allyl methyl...

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Chemoselective sp2-sp3 Cross-Couplings: Iron-Catalyzed Alkyl Transfer to Dihaloaromatics

Pamela S. Seng, Sushant Malhotra, Alan J. Deese, Kevin A. Ford, Stefan G. Koenig
Org. Lett. | 2013 | 10.1021/ol401508u

The chemoselective functionalization of a range of dihaloaromatics with methyl, cyclopropyl, and higher alkyl Grignard reagents via iron-catalyzed cross-coupling is described. The site selectivity of C–X (X = halogen) activation is determined by factors such...

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A Carbaboranylmercuric Salt Catalyzed Reaction; Highly Regioselective Cycloisomerization of 1,3-Dienes

Naoto Yamasaki, Ikuo Sasaki, Shinya Shiomi, Hirofumi Yamamoto, Hiroshi Imagawa
Org. Lett. | 2012 | 10.1021/ol300678r

The combination of carbaboranylmercuric chloride (new type of bulky Lewis acid) and silver triflate efficiently catalyzes cycloisomerization of 1,3-dienes at room temperature. The catalytic system gives allyl-substituted azacycles and cycloalkanes in...

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Silver-Mediated Trifluoromethylation of Aryldiazonium Salts: Conversion of Amino Group into Trifluoromethyl Group

Yuxuan Ye, Di Qiu, Jiajie Feng, Yan Xu, Songnan Zhang, Fanyang Mo, Jianbo Wang, Guojing Ji, Yan Zhang, Xi Wang
J. Am. Chem. Soc. | 2013 | 10.1021/ja4056239

A novel strategy for aromatic trifluoromethylation by converting aromatic amino group into CF 3 group is reported herein. This method, which can be considered as trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available...

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Fluorous Triphasic Reactions:  Transportative Deprotection of Fluorous Silyl Ethers with Concomitant Purification

Hiroyuki Nakamura, Dennis P. Curran, Bruno Linclau
J. Am. Chem. Soc. | 2001 | 10.1021/ja011716c

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Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts  [J. Am. Chem. Soc. 2000, 122, 8168−8179]. 

Steven B. Garber, Brian L. Gray, Amir H. Hoveyda, Jason S. Kingsbury
J. Am. Chem. Soc. | 2001 | 10.1021/ja0151448

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Laser-Assisted High-Pressure Chemical Reactions

Roberto Bini
Acc. Chem. Res. | 2004 | 10.1021/ar030015c

The growing need for production methods with a reduced environmental impact drives the search for new synthetic approaches in chemistry. Here we report the state of the art of a recently developed branch of ultra-high-pressure chemistry, employing high...

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New Electrophilic Difluoromethylating Reagent

George A. Olah, G. K. Surya Prakash, Csaba Weber, Sujith Chacko
Org. Lett. | 2007 | 10.1021/ol070195g

A new electrophilic difluoromethylating reagent has been developed. The S-(difluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic difluoromethyl group into the following nucleophiles:  sulfonic...

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Trichlorophenyl Formate: Highly Reactive and Easily Accessible Crystalline CO Surrogate for Palladium-Catalyzed Carbonylation of Aryl/Alkenyl Halides and Triflates

Kei Manabe, Tsuyoshi Ueda, Hideyuki Konishi
Org. Lett. | 2012 | 10.1021/ol302593z

The high utility of 2,4,6-trichlorophenyl formate, a highly reactive and easily accessible crystalline CO surrogate, is demonstrated. The decarbonylation with NEt 3 to generate CO proceeded rapidly at rt, thereby allowing external-CO-free Pd-catalyzed...

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Second-Generation Tags for Fluorous Chemistry Exemplified with a New Fluorous Mitsunobu Reagent†

Christopher Henry, Qianli Chu, Dennis P. Curran
Org. Lett. | 2008 | 10.1021/ol800750q

A new fluorous DEAD reagent bearing two perfluoro-tert-butyloxy groups with propylene spacers shows excellent promise for use in fluorous Mitsunobu reactions. Pure target products were obtained in good yields after removing fluorous byproducts by FSPE. The...

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New Method Based on 1-(Trimethysilyl)alk-1-yne To Prepare 1,4-Skipped Diynes

Florian Montel, Sebastian Wendeborn, Jilali Kessabi, Pierre M. J. Jung, Benjamin Martin, Renaud Beaudegnies, Eric Muller
Org. Lett. | 2006 | 10.1021/ol0604670

We have developed a novel reaction between a terminal TMS-alkyne and a propargyl halide in the presence of a fluoride source and a catalytic amount of copper iodide to prepare 1,4-skipped diynes with good yields and in mild conditions. We have shown that this...

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Photorelease of Primary Aliphatic and Aromatic Amines by Visible-Light-Induced Electron Transfer

Liam P. Spencer, James M. Boncella, Joseph B. Edson
Org. Lett. | 2011 | 10.1021/ol202456d

Visible-light-absorbing tris(bipyridyl)ruthenium(II) has been used to mediate electron transfer to N-methylpicolinium carbamates that undergo C–O bond fragmentation followed by spontaneous carbon dioxide release to give free amines. Release of several...

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Selective Oxoammonium Salt Oxidations of Alcohols to Aldehydes and Aldehydes to Carboxylic Acids

Nyle B. Blanck, Joseph C. Qiu, James M. Bobbitt, William F. Bailey, Priya P. Pradhan
Org. Lett. | 2011 | 10.1021/ol203096f

The oxidation of alcohols to aldehydes using stoichiometric 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in CH 2 Cl 2 at room temperature is a highly selective process favoring reaction at the carbinol center best able to...

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Application of Tin and Nanometer Tin in Allylation of Carbonyl Compounds in Tap Water

Cunliu Zhou, Zhiyong Wang, Zhenggen Zha
Org. Lett. | 2002 | 10.1021/ol0257326

Nanometer tin-mediated allylation of aldehydes or ketones in distilled or tap water gave rise to corresponding homoallyl alcohol in high yield without any other assistance such as heat or supersonic or acidic media.

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High Efficiency Synthesis of F-18 Fluoromethyl Ethers: An Attractive Alternative for C-11 Methyl Groups in Positron Emission Tomography Radiopharmaceuticals

Byoung Se Lee, Chansoo Park, Dae Yoon Chi
Org. Lett. | 2013 | 10.1021/ol401792n

A rapid and efficient method for the synthesis of O-fluoromethyl aliphatic and aromatic ethers is presented. This method is so mild that it can be used for the preparation of positron emission tomography (PET) radiopharmaceuticals bearing O-[ 18 ...

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