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With Tag: General Organic Chemistry

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Direct Construction of Quaternary Carbons from Tertiary Alcohols via Photoredox-Catalyzed Fragmentation of tert-Alkyl N-Phthalimidoyl Oxalates

Gregory L. Lackner, Larry E. Overman, Kyle W. Quasdorf
J. Am. Chem. Soc. | 2013 | 10.1021/ja408971t

A convenient method for the direct construction of quaternary carbons from tertiary alcohols by visible-light photoredox coupling of tert-alkyl N-phthalimidoyl oxalate intermediates with electron-deficient alkenes is reported.

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Rhodium(NHC)-Catalyzed Amination of Aryl Bromides

Sukbok Chang, Min Kim
Org. Lett. | 2010 | 10.1021/ol100437j

A rhodium-catalyzed amination reaction of aryl halides with amines has been developed with the use of a N-heterocyclic carbene (NHC) ligand (IiPr = 1,3-diisopropylimidazol-2-ylidene). The active metal species responsible for the reaction progress was...

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Ruthenium-Catalyzed Intramolecular [5 + 2] Cycloadditions

F. Dean Toste, Hong Shen, Barry M. Trost
J. Am. Chem. Soc. | 2000 | 10.1021/ja993400z

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Stereoselective 1,3-Insertions of Rhodium(II) Azavinyl Carbenes

Rakesh K. Sit, Brady T. Worrell, Stepan Chuprakov, Valery V. Fokin, Nicklas Selander
J. Am. Chem. Soc. | 2013 | 10.1021/ja408185c

Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N–H and O–H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide...

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Development of a Decarboxylative Palladation Reaction and Its Use in a Heck-type Olefination of Arene Carboxylates

Michael R. Mannion, Daisuke Tanaka, Andrew G. Myers
J. Am. Chem. Soc. | 2002 | 10.1021/ja027523m

The development of a palladium-catalyzed decarboxylative coupling reaction of arene carboxylates with olefinic substrates is described. The optimized procedure for decarboxylative palladation employs Pd(O 2 CCF 3 ) 2 as catalyst (0.2 equiv) in the presence...

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Fluorine-Assisted Selective Alkylation to Fluorinated Epoxides and Carbonyl Compounds:  Implication of Pentacoordinate Trialkylaluminum Complexes

Naoko Kagoshima, Keiji Maruoka, Takashi Ooi
J. Am. Chem. Soc. | 1997 | 10.1021/ja964113n

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cis-Dihydroxylation of Alkenes with Oxone Catalyzed by Iron Complexes of a Macrocyclic Tetraaza Ligand and Reaction Mechanism by ESI-MS Spectrometry and DFT Calculations

Toby Wai-Shan Chow, Zhen Guo, Chi-Ming Che, Jie-Sheng Huang, Yungen Liu, Ella Lai-Ming Wong
J. Am. Chem. Soc. | 2010 | 10.1021/ja100967g

[Fe III (L-N 4 Me 2 )Cl 2 ] + (1, L-N 4 Me 2 = N,N′-dimethyl-2,11-diaza[3.3](2,6)pyridinophane) is an active catalyst for cis-dihydroxylation of various types of alkenes with oxone at room temperature using limiting amounts of alkene substrates. In the...

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A General Model for Selectivity in Olefin Cross Metathesis

Robert H. Grubbs, Arnab K. Chatterjee, Tae-Lim Choi, Daniel P. Sanders
J. Am. Chem. Soc. | 2003 | 10.1021/ja0214882

In recent years, olefin cross metathesis (CM) has emerged as a powerful and convenient synthetic technique in organic chemistry; however, as a general synthetic method, CM has been limited by the lack of predictability in product selectivity and...

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Catalytic Asymmetric [4 + 1] Cycloaddition of Vinylallenes with Carbon Monoxide:  Reversal of the Induced Chirality by the Choice of Metal

Masahiro Murakami, Yoshihiko Ito, Kenichiro Itami
J. Am. Chem. Soc. | 1999 | 10.1021/ja9839365

Rhodium(I) and platinum(0) complexes having a chiral ligand, 1,2-bis(2,5-dialkylphosphorano)benzene, effected an asymmetric carbonylative [4 + 1] cycloaddition reaction of vinylallenes. Useful levels of asymmetric induction were attained even with substrates...

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New Radical Allylation Reaction of Iodides

Béatrice Quiclet-Sire, Stéphanie Seguin, Samir Z. Zard, Frédéric Le Guyader
J. Am. Chem. Soc. | 1997 | 10.1021/ja9708878

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Palladium Complex Catalyzed Acylation of Allylic Esters with Acylsilanes

Yuji Imai, Yasushi Obora, Takashi Kawamura, Yasushi Tsuji, Yasuhiro Ogawa
J. Am. Chem. Soc. | 2001 | 10.1021/ja010674p

Acylation of allylic esters (2) with acylsilanes (1) in the presence of a catalytic amount (5 mol %) of a palladium complex is reported. The reaction proceeds selectively to afford β,γ-unsaturated ketones (3) in high yields. [Pd(η 3 -C 6 H 5 CHCHCH 2 )(CF 3 ...

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Migrating Alkynes in Vinylidene Carbenoids:  An Unprecedented Route to Polyynes

Sara Eisler, Rik R. Tykwinski
J. Am. Chem. Soc. | 2000 | 10.1021/ja005557t

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Efficiency of a Ruthenium Catalyst in Metathesis Reactions of Sulfur-Containing Compounds

Steven P. Nolan, Gaëlle Spagnol, Marie-Pierre Heck, Charles Mioskowski
Org. Lett. | 2002 | 10.1021/ol025834w

1,3-Dimesitylimidazol-2-ylidene ruthenium benzylidene catalyst (RuCl 2 (C(H)Ph)(PCy 3 )(IMes)) has been successfully employed in ring-closing metathesis reactions of acyclic diene sulfides, disulfides, and dithianes and in self-cross metathesis reactions of...

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Free-Radical Variant for the Synthesis of Functionalized 1,5-Diketones

Samir Z. Zard, Sunggak Kim, Kelvin Kau Kiat Goh
Org. Lett. | 2013 | 10.1021/ol402213k

A free-radical approach for the synthesis of functionalized 1,5-diketones has been accomplished through an effective combination play between alkenylacylphosphonates and keto-xanthates as radical surrogates of enolates and enones, respectively.

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Practical Asymmetric Henry Reaction Catalyzed by a Chiral Diamine-Cu(OAc)2 Complex

Masahiko Watanabe, Takayoshi Arai, Akira Yanagisawa
Org. Lett. | 2007 | 10.1021/ol7014362

The chiral diamine ligand 3 was designed and synthesized from (R,R)-1,2-diphenylethylenediamine, (S)-2,2‘-dibromomethyl-1,1‘-binaphthalene, and o-xylylene dibromide. The resulting 3-Cu(OAc) 2 complex was a highly efficient catalyst for the Henry reaction,...

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A Solid-Phase Route to N-Cyanoamides

Nicholas C. Ray, David M. Parry, Trevor Morgan
Org. Lett. | 2002 | 10.1021/ol0172020

A new method for the solid-phase synthesis of cyanamides is described. The attachment of a secondary amine to solid support is accomplished using Merrifield resin. After functionalization, cleavage is readily achieved with cyanogen bromide to afford the...

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Stereoselective Formation of Trisubstituted (Z)-Chloroalkenes Adjacent to a Tertiary Carbon Stereogenic Center by Organocuprate-Mediated Reduction/Alkylation

Shunsuke Seike, Tetsuo Narumi, Haruo Aikawa, Hirokazu Tamamura, Takuya Kobayakawa
Org. Lett. | 2012 | 10.1021/ol301988d

A robust and efficient method for the synthesis of trisubstituted (Z)-chloroalkenes is described. A one-pot reaction of γ,γ-dichloro-α,β-enoyl sultams involving organocuprate-mediated reduction/asymmetric alkylation affords α-chiral (Z)-chloroalkene...

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Nickel-Catalyzed Diastereoselective Alkyl–Alkyl Kumada Coupling Reactions

Thomas Di Franco, Alessio Orsino, Peng Ren, Xile Hu, Pablo M. Perez Garcia
Org. Lett. | 2012 | 10.1021/ol302067b

A nickel pincer complex is found to catalyze alkyl–alkyl Kumada coupling reactions of 1,3- and 1,4-substituted cyclohexyl halides and tetrahydropyrans with an excellent diastereoselectivity. The mechanistic investigation of the coupling reactions provides...

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Hydrophobic Polymer-Supported Catalyst for Organic Reactions in Water:  Acid-Catalyzed Hydrolysis of Thioesters and Transprotection of Thiols

Shinya Iimura, Shū Kobayashi, Kei Manabe
Org. Lett. | 2002 | 10.1021/ol026906m

A hydrophobic polystyrene-supported sulfonic acid was found to be effective for hydrolysis of thioesters in pure water. It was revealed that the catalyst was much superior to other Brønsted acid catalysts. Transprotection of thiols from thioesters to...

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Asymmetric Hydrogenation of Alkenyl, Cyclopropyl, and Aryl Ketones. RuCl2(xylbinap)(1,2-diamine) as a Precatalyst Exhibiting a Wide Scope

Takeshi Ohkuma, Eiji Katayama, Takao Ikariya, Masatoshi Koizumi, Trang Pham, Kunihiko Murata, Henri Doucet, Masami Kozawa, Tohru Yokozawa, Ryoji Noyori
J. Am. Chem. Soc. | 1998 | 10.1021/ja983257u

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