With Tag: General Chemistry

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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...


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,...


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...


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...


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...


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...


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,...


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



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.


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.


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...


Ruthenium-Catalyzed Intramolecular [5 + 2] Cycloadditions

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



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...


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...


Doping the Golden Cage Au16- with Si, Ge, and Sn

Xiao Cheng Zeng, Lei-Ming Wang, Satya Bulusu, Wei Huang, Lai-Sheng Wang, Rhitankar Pal
J. Am. Chem. Soc. | 2007 | 10.1021/ja077465a

We report a joint experimental/theoretical study of a series of group IV atom-doped gold anion clusters MAu 16 - (M = Si, Ge, Sn). We find that their global minima possess exohedral structures, which are dominated by the strong M−Au local interactions...


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



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...


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...


Research in atmospheric chemistry and transport

Yuk L Yung


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