Papers

With Tag: General Organic Chemistry

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Monitoring Supramolecular Self-Assembly using Time-Resolved Fluorescence Spectroscopy

Australian Journal of Chemistry | 2011 | 10.1071/CH11066

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Low-Valent Ruthenium and Iridium Hydride Complexes as Alternatives to Lewis Acid and Base Catalysts

Shun-Ichi Murahashi, Hikaru Takaya
Acc. Chem. Res. | 2000 | 10.1021/ar980085x

The discovery of a new chemical reaction often leads to new applications and new chemical principles. Low-valent ruthenium and iridium hydride complexes are highly useful redox Lewis acid and base catalysts. Nitriles are activated by these catalysts and...

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Selective Fluoroalkylations with Fluorinated Sulfones, Sulfoxides, and Sulfides†

G. K. Surya Prakash, Jinbo Hu
Acc. Chem. Res. | 2007 | 10.1021/ar700149s

Efficient fluoroalkylations have been proven to be a highly useful strategy for the synthesis of bioactive fluorine-containing compounds and other materials. The design and use of a single category of reagents for multiple synthetic goals are much more...

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Improving instructional design with better analysis of assessment data

2014 | 10.5204/jld.v7i2.199

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A Metal–Organic Framework with a Hierarchical System of Pores and Tetrahedral Building Blocks

Angewandte Chemie | 2006 | 10.1002/ange.200600175

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(2,7-Disubstituted-1,8-biphenylenedioxy)bis(dimethylaluminum) as Bidentate Organoaluminum Lewis Acids:  Elucidation and Synthetic Utility of the Double Electrophilic Activation Phenomenon

Takashi Ooi, Makoto Takahashi, Masao Yamada, Eiji Tayama, Kiyoyuki Omoto, Keiji Maruoka
Journal of American Chemical Society | 2004 | 10.1021/ja030552s

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A Novel Cycloisomerization of Tetraenones:  4+3 Trapping of the Nazarov Oxyallyl Intermediate

Yong Wang, Atta M. Arif, F. G. West
Journal of American Chemical Society | 1999 | 10.1021/ja9837001

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Continuous Flow Coupling and Decarboxylation Reactions Promoted by Copper Tubing

Sejal Patel, Timothy F. Jamison, Nello Mainolfi, Yun Zhang
Org. Lett. | 2010 | 10.1021/ol1026848

A convenient and efficient flow method for Ullmann condensations, Sonogashira couplings, and decarboxylation reactions using a commercially available copper tube flow reactor (CTFR) is described. The heated CTFR effects these transformations without added...

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Copper-Catalyzed Trifluoromethylation of Aryl and Vinyl Boronic Acids with An Electrophilic Trifluoromethylating Reagent

Tianfei Liu, Qilong Shen
Org. Lett. | 2011 | 10.1021/ol2005903

A copper-catalyzed trifluoromethylation of aryl- and alkenylboronic acids with Togni’s reagent was described. The reaction proceeded in good to excellent yields for a range of different substrates including heteroarylboronic acids and substrates with a...

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A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence

Damien Webb, Timothy F. Jamison
Org. Lett. | 2012 | 10.1021/ol300722e

A continuous protocol for the two-carbon homologation of esters to α,β-unsaturated esters is described. This multireactor homologation telescopes an ester reduction, phosphonate deprotonation, and Horner–Wadsworth–Emmons olefination, thus converting a...

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Geminal Alkene–Alkyne Cross Metathesis Using a Relay Strategy

Joseph R. Clark, Edgars Jecs, Steven T. Diver, Jonathan M. French
Org. Lett. | 2012 | 10.1021/ol301846q

A relay strategy was employed to achieve an intermolecular ene–yne metathesis between 1,1-disubstituted alkenes and alkynes. The relay serves to activate an unreactive alkene which will not participate in ene-yne metathesis. The new relay cross ene–yne...

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Highly Enantioselective Ketone-Ene Reactions of Trifluoropyruvate: Significant Counterion Effect of the In(III)−PyBox Complex

Boon-Hong Tan, Teck-Peng Loh, Jun-Feng Zhao, Teguh-Budiono W. Tjan
Org. Lett. | 2009 | 10.1021/ol902507x

A chiral indium(III)−pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to...

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Organocatalytic Asymmetric Michael-Type/Wittig Reaction of Phosphorus Ylides: Synthesis of Chiral α-Methylene-δ-Ketoesters

Haibin Mao, Chengjian Zhu, Aijun Lin, Huiming Ge, Yixiang Cheng, Renxiang Tan, Junying Wang
Org. Lett. | 2011 | 10.1021/ol201483s

An asymmetric Michael-type reaction of phosphorus ylides and α,β-unsaturated ketones under the catalysis of a chiral ion pair catalyst has been described. The ion pair catalyst containing a chiral counteranion was prepared by simply mixing...

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Deacylative Oxidation Strategy for the Preparation of α-Functionalized Carbonyls

J. Du Bois, Benjamin H. Brodsky
Org. Lett. | 2004 | 10.1021/ol040039z

α-Alkoxylation and amination of carbonyl derivatives is made possible through a unique deacylative coupling reaction that proceeds via in situ Rh-carbene formation and subsequent heteroatom-H (X−H) insertion. Reactions perform optimally with five- and...

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Copper(I)-Catalyzed Carboxylation of Aryl- and Alkenylboronic Esters

Jun Takaya, Satoshi Tadami, Kazutoshi Ukai, Nobuharu Iwasawa
Org. Lett. | 2008 | 10.1021/ol800829q

The copper(I)-catalyzed carboxylation reaction of aryl- and alkenylboronic esters proceeded smoothly under CO 2 to give the corresponding carboxylic acid in good yield. This reaction showed wide generality with higher functional group tolerance compared to...

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Palladium-Catalyzed Formal Hydroacylation of Allenes Employing Acid Chlorides and Hydrosilanes

Kenta Tatsumi, Tetsuaki Fujihara, Yasushi Tsuji, Jun Terao
Org. Lett. | 2013 | 10.1021/ol400862k

The palladium-catalyzed formal hydroacylation of allenes employing acid chlorides and hydrosilanes has been achieved. The reactions proceed with commercially available Pd(OAc) 2 as a catalyst and HSi(iPr) 3 as a reducing reagent, giving the corresponding...

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1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains

Yohan Georges, Mar Vicente, Xavier Ariza, Jordi Garcia
Org. Lett. | 2006 | 10.1021/ol0616539

(R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality...

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Cobalt-Catalyzed Arylzincation of Alkynes

Koichiro Oshima, Hideki Yorimitsu, Kei Murakami
Org. Lett. | 2009 | 10.1021/ol900883j

Cobalt(II) bromide catalyzes arylzincation of alkynes with arylzinc iodide•lithium chloride complexes in acetonitrile. The scope of the arylzincation is wide enough to use unfunctionalized alkynes, such as 6-dodecyne, as well as arylacetylenes. The inherent...

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Direct Transfer of the Sulfonylimino Group of Imino-λ3-Bromane to N-Heterocycles and Trialkylamines: Synthesis of N-Iminoammonium Ylides under Metal-Free Conditions

Takao Kaneaki, Masahito Ochiai, Norihiro Tada, Yufuko Kawano, Kazunori Miyamoto
Org. Lett. | 2008 | 10.1021/ol802383f

Exposure of N-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-λ 3 -bromane at room temperature results in direct transfer of the sulfonylimino group to the nitrogen atoms and affords a variety of iminoammonium ylides under...

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Highly Practical and Enantioselective Cu-Catalyzed Conjugate Addition of Alkylzinc Reagents to Cyclic Enones at Ambient Temperature

Isaac J. Krauss, James L. Leighton
Org. Lett. | 2003 | 10.1021/ol034983r

A new ligand for Cu-catalyzed enantioselective additions of dialkylzincs to cyclic enones has been developed. In addition to providing good to excellent enantioselectivities with a range of cyclic enones and dialkylzincs, the ligand has several notworthy...

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