With Tag: General Chemistry

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Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides

Ian K. Mangion, Mark A. Huffman, Michael Shevlin, Ikenna K. Nwamba
Org. Lett. | 2009 | 10.1021/ol901298p

The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X−H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular...


Iridium-Catalyzed Coupling Reaction of Primary Alcohols with 1-Aryl-1-propynes Leading to Secondary Homoallylic Alcohols

Shintaro Hatanaka, Yasutaka Ishii, Yasushi Obora
Org. Lett. | 2009 | 10.1021/ol901366q

We report iridium-catalyzed coupling of 2-alkynes such as 1-aryl-1-propynes with primary alcohols leading to secondary homoallylic alcohols as products. This reaction involves an iridium-catalyzed novel catalytic transformation of 2-alkynes and primary...


New Catalytic Cycle for Couplings of Aldehydes with Organochromium Reagents

Kosuke Namba, Yoshito Kishi
Org. Lett. | 2004 | 10.1021/ol047661b

A new catalytic cycle has been developed to effect all three subgroups of Cr-mediated couplings, i.e., (1) Ni/Cr-mediated alkenylation, alkynylation, and arylation, (2) Co/Cr-mediated 2-haloallylation, alkylation, and propargylation, and (3) Cr-mediated...


Rh-Catalyzed Reductive Coupling Reaction of Aldehydes with Conjugated Dienes Promoted by Triethylborane

Masanari Kimura, Masahiro Fukushima, Yoshio Inoue, Yusuke Sonoda, Shuichi Oi, Daisuke Nojiri
Org. Lett. | 2009 | 10.1021/ol901527b

Rh(I) catalyzes the reductive coupling reaction of a wide variety of aldehydes with conjugated dienes in the presence of a stoichiometric amount of triethylborane to provide homoallyl alcohols in a single operation.


Silver-Catalyzed Difunctionalization of Terminal Alkynes: Highly Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates

Yibiao Li, Zhengwang Chen, Huanfeng Jiang, Shifa Zhu, Jinghao Li, Chaorong Qi
Org. Lett. | 2010 | 10.1021/ol101251n

A new silver-catalyzed highly regio- and stereoselective difunctionalization reaction of simple terminal alkynes was reported in which the (Z)-β-haloenol acetate derivatives were formed efficiently. The resulting products were versatile intermediates in...


A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates

John F. Hartwig, Daniel W. Robbins
Org. Lett. | 2012 | 10.1021/ol301570t

A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by...


Aminomethylations via Cross-Coupling of Potassium Organotrifluoroborates with Aryl Bromides

Deidre L. Sandrock, Gary A. Molander
Org. Lett. | 2007 | 10.1021/ol070543e

The Suzuki−Miyaura cross-coupling reaction of N,N-dialkylaminomethyltrifluoroborates with aryl halides allows the construction of an aminomethyl aryl linkage through a disconnection based on dissonant reactivity patterns. A variety of these...


Siloxyl Ether Functionalized Resins for Chemoselective Enrichment of Carboxylic Acids

Erin E. Carlson, Darci J. Trader
Org. Lett. | 2011 | 10.1021/ol202376m

Although the carboxylic acid moiety is prevalent in many biologically produced molecules, including natural products and proteins, methods to chemoselectively target this functional group have remained elusive. Generally, strategies that utilize carboxylate...


Selective Alkylation of Amines with Alcohols by Cp*–Iridium(III) Half-Sandwich Complexes

Frank Rominger, Mathias Schelwies, Marion K. Brinks, Michael Limbach, Simone Wöckel, Alexander Wetzel, Peter Hofmann
Org. Lett. | 2013 | 10.1021/ol303075h

[Cp*Ir(Pro)Cl] (Pro = prolinato) was identified among a series of Cp*–iridium half-sandwich complexes as a highly reactive and selective catalyst for the alkylation of amines with alcohols. It is active under mild conditions in either toluene or water without...


Tetra-ortho-Substituted Biaryls through Palladium-Catalyzed Suzuki−Miyaura Couplings with a Diaminochlorophosphine Ligand

Lutz Ackermann, Robert Born, Peter Mayer, Harish K. Potukuchi, Andreas Althammer
Org. Lett. | 2010 | 10.1021/ol1000186

A palladium complex derived from a sterically hindered diaminochlorophosphine allowed for Suzuki−Miyaura cross-couplings of chloroarenes with ample scope and provided access to tetra-ortho-substituted bi(hetero)aryls.


A Straightforward Protocol for One-Pot Allylic Aminations/Stille Couplings

Christian Bukovec, Uli Kazmaier
Org. Lett. | 2009 | 10.1021/ol901415p

Stannylated allylic carbonates are suitable substrates for Pd-catalyzed allylic aminations. In DMF and with [Pd(allyl)Cl] 2 as catalyst, the stannylated allyl amines formed can be directly coupled with electrophiles according to the Stille protocol, giving...


Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes

Christopher A. Russell, Liam T. Ball, Michael Green, Guy C. Lloyd-Jones
Org. Lett. | 2010 | 10.1021/ol1019162

Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph 3 PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions proceed...


Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis

Munetaka Akita, Yusuke Yasu, Takashi Koike
Org. Lett. | 2013 | 10.1021/ol4006272

Intermolecular aminotrifluoromethylation of alkenes catalyzed by [Ru(bpy) 3 ] 2+ under visible light irradiation has been explored. The present photocatalytic protocol achieves highly efficient and regioselective difunctionalization of C═C bonds, leading to...


A Convenient Preparation of 2-Fluoro-3-alkoxy-1,3-butadienes

James Rogers, Timothy B. Patrick, Keith Gorrell
Org. Lett. | 2002 | 10.1021/ol026512v

1-Chloro-1-fluoro-2-methoxy-2-methylcyclopropane eliminates HCl on heating in quinoline solution above 50 °C to give 2-fluoro-3-methoxy-1,3-butadiene in high yield. If an alcohol is added to the reaction then a 2-fluoro-3-alkoxy-1,3-butadiene is obtained in...


Primary Amine, Thiourea-Based Dual Catalysis Motif for Synthesis of Stereogenic, All-Carbon Quaternary Center-Containing Cycloalkanones

Jun Yong Kang, Rich G. Carter
Org. Lett. | 2012 | 10.1021/ol301272r

The enantioselective synthesis of α,α-disubstituted cycloalkanones has been developed using a primary amine, thiourea-based dual catalysis pathway. A range of electrophiles and ring sizes are tolerated under the reaction conditions. A possible catalytic cycle...


Highly Enantioselective Titanium-Catalyzed Cyanation of Imines at Room Temperature

Abdul Majeed Seayad, Takushi Nagata, Balamurugan Ramalingam, Kazuhiko Yoshinaga, Christina L. L. Chai
Org. Lett. | 2009 | 10.1021/ol902540h

A highly active and enantioselective titanium-catalyzed cyanation of imines at room temperature is described. The catalyst used is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand....


A Magnetic Biomimetic Nanocatalyst for Cleaving Phosphoester and Carboxylic Ester Bonds under Mild Conditions

Chuansong Duanmu, Yong Gao, Yan Zheng
Org. Lett. | 2006 | 10.1021/ol061098a

As a result of the unique surface structure of nanospheres, Asp and His residues supported on a 12 nm maghemite nanoparticle worked collaboratively as a biomimetic nanocatalyst for hydrolyzing paraoxon (phosphoester) and 4-nitrophenyl acetate (carboxylic...


Sequential Reactions with Grubbs Catalyst and AD-mix-α/β Using PDMS Thimbles

Michael D. Schulz, Martin T. Mwangi, Ned B. Bowden
Org. Lett. | 2008 | 10.1021/ol8022215

Incompatible Grubbs catalyst and an osmium dihydroxylation catalyst were site-isolated from each other using polydimethylsiloxane thimbles. The Grubbs catalyst was added to the interior of the thimbles, and AD-mix-α/β was added to the exterior. Organic...


Palladium-Catalyzed Catellani Aminocyclopropanation Reactions with Vinyl Halides

Avinash Khanna, David L. Van Vranken, Ilandari Dewage Udara Anulal Premachandra, Paul D. Sung
Org. Lett. | 2013 | 10.1021/ol401383m

Palladium is shown to catalyze an intramolecular aminocyclopropanation of norbornenes with aliphatic vinyl halides in good yields. The reaction tolerates a variety of amine substituents and gives good results with a variety of carbocyclic and oxabicyclic...


Copper/Ascorbic Acid Dyad as a Catalytic System for Selective Aerobic Oxidation of Amines

Svatava Voltrova, Jiri Srogl
Org. Lett. | 2009 | 10.1021/ol802715c

A new, environmentally benign system based on an ascorbic acid (vitamin C)/copper dyad is presented, which facilitates the oxidation of amines to carbonyl compounds. The oxidation utilizes aerobic oxygen as the ultimate electron scavenger, which accepts...

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