56667-11-9Relevant academic research and scientific papers
E, Z -Selectivity in the reductive cross-coupling of two benzaldehydes to stilbenes under substrate control
Arkhypchuk, Anna I.,D'Imperio, Nicolas,Ott, Sascha
supporting information, p. 6171 - 6179 (2020/10/21)
Unsymmetrical E- and Z-stilbenes can be synthesized from two differently substituted benzaldehydes in a MesP(TMS)Li-promoted reductive coupling sequence. Depending on the order of addition of the two coupling partners, the same olefin can be produced in either E- or Z-enriched form under identical reaction conditions. A systematic study of the correlation between the stereochemical outcome of the reaction and the substitution pattern at the two aldehydes is presented. The results can be used as guidelines to predict the product stereochemistry. This journal is
Copper-catalyzed double intramolecular ullmann coupling for the synthesis of diastereomerically and enantiomerically pure 4b,9b-dihydrobenzofuro[3,2-b]benzofurans
Imrich, Hans-Georg,Conrad, Jürgen,Beifuss, Uwe
, p. 7718 - 7734 (2015/12/31)
The copper-catalyzed double intramolecular Ullmann coupling of syn-1,2-bis(2-bromoaryl)ethane-1,2-diols with catalytic amounts of CuII oxinate as the copper source, K3PO4 as a base, and KI as a reductant in aqueous acetoni
Synthesis of a guanidine NHC complex and its application in borylation reactions
Tai, Chia-Cheng,Yu, Ming-Shiuan,Chen, Yi-Lin,Chuang, Wen-Hang,Lin, Ting-Hua,Yap, Glenn P. A.,Ong, Tiow-Gan
supporting information, p. 4344 - 4346 (2014/04/17)
Synthesis of guanidine-linked NHC can be achieved easily through reacting amino-NHC with carbodiimide. Subsequently, guanidine-NHC Ag and Cu complexes were isolated and fully characterized. These Cu complexes are found to be versatile catalysts for hydroboration, semihydrogenation and carboboration of alkynes in a highly stereo- and regioselective fashion.
Unequivocal experimental evidence for a unified lithium salt-free wittig reaction mechanism for all phosphonium ylide types: Reactions with β-heteroatom-substituted aldehydes are consistently selective for cis-oxaphosphetane-derived products
Byrne, Peter A.,Gilheany, Declan G.
, p. 9225 - 9239 (2012/07/14)
The true course of the lithium salt-free Wittig reaction has long been a contentious issue in organic chemistry. Herein we report an experimental effect that is common to the Wittig reactions of all of the three major phosphonium ylide classes (non-stabilized, semi-stabilized, and stabilized): there is consistently increased selectivity for cis-oxaphosphetane and its derived products (Z-alkene and erythro-β-hydroxyphosphonium salt) in reactions involving aldehydes bearing heteroatom substituents in the β-position. The effect operates with both benzaldehydes and aliphatic aldehydes and is shown not to operate in the absence of the heteroatom substituent on the aldehyde. The discovery of an effect that is common to reactions of all ylide types strongly argues for the operation of a common mechanism in all Li salt-free Wittig reactions. In addition, the results are shown to be most easily explained by the [2+2] cycloaddition mechanism proposed by Vedejs and co-workers as supplemented by Aggarwal, Harvey, and co-workers, thus providing strong confirmatory evidence in support of that mechanism. Notably, a cooperative effect of ortho-substituents in the case of semi-stabilized ylides is confirmed and is accommodated by the cycloaddition mechanism. The effect is also shown to operate in reactions of triphenylphosphine-derived ylides and has previously been observed for reactions under aqueous conditions, thus for the first time providing evidence that kinetic control is in operation in both of these cases.
Palladium-catalyzed double N-arylation to synthesize multisubstituted dibenzoazepine derivatives
Zhang, Xiaoyun,Yang, Yuan,Liang, Yun
, p. 6406 - 6408,3 (2012/12/12)
Palladium-catalyzed double N-arylation of primary amines with (Z)-1,2-bis(2-bromophenyl)ethenes was investigated. A variety of dibenzoazepine derivatives were synthesized in good to excellent yields.
Aluminepin: Aluminum analogues of borepin and gallepin
Yoshida, Kengo,Furuyama, Taniyuki,Wang, Chao,Muranaka, Atsuya,Hashizume, Daisuke,Yasuike, Shuji,Uchiyama, Masanobu
, p. 729 - 732 (2012/03/26)
We report synthesis of dibenzoaluminepin as the first aluminepin, an aluminum analogue of borepin and gallepin. This compound contains one molecule of ethereal solvent on the Al atom, which adopts a tetrahedral geometry. The central 7-membered aluminepin
Construction of benzosiloles, six- and eight-membered silacyclic skeletons, via a Pd-catalyzed intramolecular Mizoroki-Heck reaction of vinylsilanes
Ouyang, Kunbing,Liang, Yun,Xi, Zhenfeng
supporting information, p. 4572 - 4575 (2012/11/07)
A variety of silacycles including benzosiloles, six- and eight-membered silacyclic skeletons, were efficiently synthesized via a Pd-catalyzed intramolecular Mizoroki-Heck reaction of vinylsilanes.
Synthesis of functionalizable boron-containing π-electron materials that incorporate formally aromatic fused borepin rings
Caruso Jr., Anthony,Siegler, Maxime A.,Tovar, John D.
scheme or table, p. 4213 - 4217 (2010/08/07)
(Figure Presented) Not a natty B-OH: Borepin-based extended π-electron molecules contain bulky substituents that shield the vacant boron p orbitals and allow synthetic manipulation and purification under ambient conditions. These borepin-containing compounds (see picture; Mes* = 1,3,5-tris(tert-butyl) phenyl; B orange, C gray) display reversible cathodic electrochemistry and can be viewed as n-type analogues to bent acene hydrocarbons.
Allenes in asymmetric catalysis: Asymmetric ring opening of meso-epoxides catalyzed by allene-containing phosphine oxides
Pu, Xiaotao,Qi, Xiangbing,Ready, Joseph M.
supporting information; experimental part, p. 10364 - 10365 (2009/12/03)
(Chemical Equation Presented) Unsymmetrically substituted allenes (1,2-dienes) are inherently chiral and can be prepared in optically pure form. Nonetheless, to date the allene framework has not been incorporated into ligands for asymmetric catalysis. Since allenes project functionality differently than either tetrahedral carbon or chiral biaryls, they may create complementary chiral environments. This study demonstrates that optically active, C 2-symmetric allene-containing bisphosphine oxides can catalyze the addition of SiCl4 to meso-epoxides with high enantioselectivity. The epoxide opening likely involves generation of a Lewis acidic, cationic (bisphosphine oxide)SiCl3 complex. The fact that high asymmetric induction is observed suggests that allenes may represent a new platform for the development of ligands and catalysts for asymmetric synthesis.
