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



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...


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...


Improving instructional design with better analysis of assessment data

2014 | 10.5204/jld.v7i2.199



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

Angewandte Chemie | 2006 | 10.1002/ange.200600175



(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



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



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...


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...


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...


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...


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...


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...


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...


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...


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...


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...


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...


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...


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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