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With Tag: General Organic Chemistry

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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...

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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...

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Ketone Synthesis under Neutral Conditions. Cu(I) Diphenylphosphinate-Mediated, Palladium-Catalyzed Coupling of Thiol Esters and Organostannanes

Rüdiger Wittenberg, Jiri Srogl, Lanny S. Liebeskind, Masahiro Egi
Org. Lett. | 2003 | 10.1021/ol034962x

A versatile approach to ketone synthesis is described. The reaction relies on the palladium-catalyzed, copper diphenylphosphinate-mediated coupling of thiol esters with organostannanes under neutral reaction conditions. This reaction complements the...

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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...

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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....

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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...

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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...

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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...

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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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Catalytic Intermolecular Allylic C—H Alkylation

Andrew J. Young, M. Christina White
J. Am. Chem. Soc. | 2008 | 10.1021/ja806867p

The first electrophilic Pd(II)-catalyzed allylic C—H alkylation is reported, providing a novel method for formation of sp 3 −sp 3 C—C bonds directly from C—H bonds. A wide range of aromatic and heteroaromatic linear (E)-α-nitro-arylpentenoates are obtained...

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Cyanuric Chloride as a Mild and Active Beckmann Rearrangement Catalyst

Hisashi Yamamoto, Yoshiro Furuya, Kazuaki Ishihara
J. Am. Chem. Soc. | 2005 | 10.1021/ja053441x

The first general organocatalytic Beckmann rearrangement of ketoximes into amides has been realized by the catalytic use of cyanuric chloride. Furthermore, acids such as HCl and ZnCl 2 are effective as cocatalysts with cyanuric chloride. For example,...

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Ligand-Free Ni-Catalyzed Reductive Cleavage of Inert Carbon–Sulfur Bonds

Ruben Martin, Nekane Barbero
Org. Lett. | 2012 | 10.1021/ol2033306

A catalytic reductive cleavage of C(sp 2 )– and C(sp 3 )–SMe bonds under ligandless conditions is presented. The method is characterized by its wide scope and high chemoselectivity profile including challenging substrate combinations, allowing the design of...

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Epoxide Hydrolase-Catalyzed Enantioselective Synthesis of Chiral 1,2-Diols via Desymmetrization of meso-Epoxides

Bin Han, Zuolin Zhu, David P. Weiner, Hongjun Huang, Zilin Huang, Dan E. Robertson, Dan S. Malashock, Aileen Milan, Lishan Zhao, Mark Miller, Mark J. Burk
J. Am. Chem. Soc. | 2004 | 10.1021/ja0466210

The discovery, from nature, of a diverse set of microbial epoxide hydrolases is reported. The utility of a library of epoxide hydrolases in the synthesis of chiral 1,2-diols via desymmetrization of a wide range of meso-epoxides, including cyclic as well as...

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Rhodium-Catalyzed Reductive Cleavage of Carbon−Cyano Bonds with Hydrosilane: A Catalytic Protocol for Removal of Cyano Groups

Yusuke Kita, Naoto Chatani, Mamoru Tobisu, Ryo Nakamura
J. Am. Chem. Soc. | 2009 | 10.1021/ja810142v

The rhodium-catalyzed reductive cleavage of carbon−cyano bonds is developed using hydrosilane as a mild reducing agent. A wide range of nitriles, including aryl, benzyl, and β-hydrogen containing alkyl cyanides are applicable to this decyanation reaction. The...

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Reaction of Unstabilized Iodonium Ylides with Organoboranes

Masahito Ochiai, Yoshimi Tuchimoto, Nobuyuki Higashiura
Org. Lett. | 2004 | 10.1021/ol0495669

Exposure of monocarbonyl iodonium ylides, generated by the ester exchange of (Z)-(2-acetoxyvinyl)-λ 3 -iodanes with EtOLi, to organoboranes results in a 1,2-shift of a carbon ligand from boron to the ylide carbons, which probably generates hitherto...

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Controllable Diastereoselective Cyclopropanation. Enantioselective Synthesis of Vinylcyclopropanes via Chiral Telluronium Ylides

Wei-Wei Liao, Kai Li, Yong Tang
J. Am. Chem. Soc. | 2003 | 10.1021/ja036254c

Novel chiral telluronium salts 1 are designed for asymmetric synthesis of 1,3-disubstituted 2-vinylcyclopropanes. The allylides, generated in situ from the corresponding telluronium salt in the presence of different base, reacted with α,β-unsaturated esters,...

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A New Stereoselective Method for the Preparation of Allylic Alcohols

Eric Oblinger, John Montgomery
J. Am. Chem. Soc. | 1997 | 10.1021/ja9719182

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Enantioselective Aldol Reactions Catalyzed by Tin Methoxide and BINAP·Silver(I) Complex

Hisashi Yamamoto, Kenichi Asakawa, Yukari Matsumoto, Akira Yanagisawa
J. Am. Chem. Soc. | 1999 | 10.1021/ja982857q

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Efficient and Z-Selective Cross-Metathesis of Conjugated Enynes

Daesung Lee, Eric C. Hansen
Org. Lett. | 2004 | 10.1021/ol049378i

The generation of a conjugated alkynyl alkylidene has been achieved using an allyl ether moiety as an intramolecular catalyst delivery vehicle. The reaction of this intermediate with alkenes and alkynes yields conjugated enynes with Z-selectivity.

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Enantioselective Synthesis of α-Stereogenic γ-Keto Esters via Formal Umpolung

Chuanfa Ni, Fang Wang, Zhe Zhang, Ralf Haiges, George A. Olah, G. K. Surya Prakash
Org. Lett. | 2012 | 10.1021/ol301112m

A feasible method has been developed for the enantioselective synthesis of α-stereogenic γ-keto esters. By employing nitro(phenylsulfonyl)methane as an acyl anion equivalent, the integrated Michael addition reaction-oxidative methanolysis protocol allows the...

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