19353-81-2Relevant academic research and scientific papers
Remote migratory cross-electrophile coupling and olefin hydroarylation reactions enabled by in situ generation of nih
Chen, Fenglin,Chen, Ke,Zhang, Yao,He, Yuli,Wang, Yi-Ming,Zhu, Shaolin
supporting information, p. 13929 - 13935 (2017/11/07)
A highly efficient strategy for remote reductive cross-electrophile coupling has been developed through the ligand-controlled nickel migration/arylation. This general protocol allows the use of abundant and bench-stable alkyl bromides and aryl bromides for the synthesis of a wide range of structurally diverse 1, 1-diarylalkanes in excellent yields and high regioselectivities under mild conditions. We also demonstrated that alkyl bromide could be replaced by the proposed olefin intermediate while using n-propyl bromide/Mn0 as a potential hydride source.
Selective Pd-catalyzed hydrogenation of 3,3-diphenylallyl alcohol: Efficient synthesis of 3,3-diarylpropylamine drugs diisopromine and feniprane
Claudino, Thiago S.,Scholten, Jackson D.,Monteiro, Adriano L.
, p. 53 - 56 (2017/09/01)
The Pd-catalyzed selective hydrogenation of C[dbnd]C double bond in (3,3-diphenylallyl)diisopropylamine or 3,3-diphenylallyl alcohol was evaluated using different catalytic systems [Pd/C, Pd(OAc)2/ionic liquid, isolated Pd(0) nanoparticles]. For the (3,3-diphenylallyl)diisopropylamine, hydrogenolysis is preferred over hydrogenation, and only moderate selectivities were obtained for the desired product. However, complete conversion and 100% selectivity were obtained for the hydrogenation of 3,3-diphenylallyl alcohol using isolated Pd(0) nanoparticles under mild condition. This successful strategy enabled the effective synthesis of diisopromine and feniprane drugs and opens new possibilities for the preparation of other biologically active compounds.
Chiral dihydrobenzo[1,4]oxazines as catalysts for the asymmetric transfer-hydrogenation of α,β-unsaturated aldehydes
Ebner, Christian,Pfaltz, Andreas
supporting information; experimental part, p. 10287 - 10290 (2012/02/01)
A new class of organocatalysts based on the structure of 2,3-dihydrobenzo[1,4]oxazine was prepared and applied in the enantioselective transfer-hydrogenation of α,β-unsaturated aldehydes with Hantzsch ester as hydride donor. These catalysts proved to be particularly effective for the conjugate reduction of β,β-diaryl-substituted acrylaldehydes leading to saturated aldehydes bearing a stereogenic center with two different aryl groups with enantioselectivities of up to 91% ee.
Iridium-catalyzed asymmetric hydrogenation yielding chiral diarylmethines with weakly coordinating or noncoordinating substituents
Tolstoy, Paeivi,Engman, Mattias,Paptchikhine, Alexander,Bergquist, Jonas,Church, Tamara L.,Leung, Abby W.-M.,Andersson, Pher G.
supporting information; experimental part, p. 8855 - 8860 (2009/12/04)
Diarylmethine-containing stereocenters are present in pharmaceuticals and natural products, making the synthetic methods that form these chiral centers are important in industry. We have applied iridium complexes with novel N,P-chelating ligands to the asymmetric hydrogenation of trisubstituted olefins, forming diarylmethine chiral centers in high conversions and excellent enantioselectivities (up to 99% ee) for a broad range of substrates. Our results support the hypothesis that steric hindrance in one specific area of the catalyst is playing a key role in stereoselection, as the hydrogenation of substrates differing little at the prochiral carbon occurred with high enantioselectivity. As a result, excellent stereodiscrimination was obtained even when the prochiral carbon bore, for example, phenyl and p-tolyl groups.
