Journal ArticleDOI
Ruthenium‐Catalyzed Cycloaddition of 1,6‐Diynes and Nitriles under Mild Conditions: Role of the Coordinating Group of Nitriles
Yoshihiko Yamamoto,Yoshihiko Yamamoto,Keisuke Kinpara,Ryuji Ogawa,Hisao Nishiyama,Kenji Itoh +5 more
TLDR
Careful screening of nitrile components revealed that a C[triple chemical bond]C triple bond or heteroatom substituents, such as methoxy and methylthio groups, proved to act as the coordinating groups, whereas C==C or C==O double bonds and amino groups failed to promote cycloaddition.Abstract:
In the presence of a catalytic amount of [Cp*RuCl(cod)] (Cp*=pentamethylcyclopentadienyl, cod=1,5-cyclooctadiene), 1,6-diynes were allowed to react chemo- and regioselectively with nitriles bearing a coordinating group, such as dicyanides or alpha-halonitriles, at ambient temperature to afford bicyclic pyridines Careful screening of nitrile components revealed that a C[triple chemical bond]C triple bond or heteroatom substituents, such as methoxy and methylthio groups, proved to act as the coordinating groups, whereas C==C or C==O double bonds and amino groups failed to promote cycloaddition This suggests that coordinating groups with multiple pi-bonds or lone pairs are essential for the nitrile componentsread more
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Journal ArticleDOI
Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles
TL;DR: The present review is a transition metal-catalyzed synthesis of aromatic monocyclic heterocycles, aiming at achieving greater levels of molecular complexity and better functional group compatibilities in a convergent and atom economical fashions from readily accessible starting materials and under mild reaction conditions.
Journal ArticleDOI
The fascinating construction of pyridine ring systems by transition metal-catalysed [2 + 2 + 2] cycloaddition reactions
Barbara Heller,Marko Hapke +1 more
TL;DR: This tutorial review is focusing on the de novo construction of pyridine ring systems by the transition metal-catalysed [2 + 2 + 2] cycloaddition reaction and the advances in the synthesis of chiral pyridines and biaryls using the cyclotrimerization method.
Journal ArticleDOI
Transition-metal-catalyzed enantioselective [2+2+2] cycloadditions for the synthesis of axially chiral biaryls.
TL;DR: The enantioselective synthesis of axially chiral biaryls possessing non-biaryl axial chirality was also developed by using chiral rhodium(I) complexes as catalysts.
Journal ArticleDOI
Mn(III)-mediated reactions of cyclopropanols with vinyl azides: synthesis of pyridine and 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives.
Yi-Feng Wang,Shunsuke Chiba +1 more
TL;DR: A Mn(III)-mediated divergent synthesis of substituted pyridines and 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives was exploited using readily available vinyl azides and cyclopropanols with a wide range of substituents.
Journal ArticleDOI
Mn(III)-Mediated Formal [3+3]-Annulation of Vinyl Azides and Cyclopropanols: A Divergent Synthesis of Azaheterocycles
TL;DR: Vinyl azides were successfully applied as a three-atom unit including one nitrogen to prepare pyridines and δ-lactams by the reactions with monocyclic cyclopropanols as well as to construct 2-azabicyclo[3.3.1].
References
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Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
TL;DR: Numerical calculations on a number of atoms, positive ions, and molecules, of both open- and closed-shell type, show that density-functional formulas for the correlation energy and correlation potential give correlation energies within a few percent.
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Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals
P. Jeffrey Hay,Willard R. Wadt +1 more
TL;DR: In this article, effective core potentials (ECP) have been derived to replace the innermost core electron for third row (K), fourth row (Rb-Ag), and fifth row (Cs-Au) atoms.
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Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules
TL;DR: In this article, two extended basis sets (termed 5-31G and 6 -31G) consisting of atomic orbitals expressed as fixed linear combinations of Gaussian functions are presented for the first row atoms carbon to fluorine.
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The influence of polarization functions on molecular orbital hydrogenation energies
P. C. Hariharan,John A. Pople +1 more
TL;DR: In this paper, a split-valence extended gaussian basis set was used to obtain the LCAO-MO-SCF energies of closed shell species with two non-hydrogen atoms.
Journal ArticleDOI
Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements
Michelle Francl,William J. Pietro,Warren J. Hehre,J. Stephen Binkley,Mark S. Gordon,Douglas J. DeFrees,John A. Pople +6 more
TL;DR: In this article, the 631G* and 6 31G* basis sets were extended through the second-row of the periodic table and the Hartree-Fock wave functions were used to obtain the equilibrium geometries for one-heavy-atom hydrides.
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Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.
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