36714-99-5

Upstream product

• 766-96-1 4-bromo-1-ethynylbenzene 
• 104-94-9 4-methoxy-aniline 
• 99-90-1 para-bromoacetophenone 

Downstream Products

• 869307-79-9 1-([1,1'-biphenyl]-4-yl)-N-(4-methoxyphenyl)ethan-1-imine 
• 1160638-10-7 C₂₁H₁₈BrNO 
• 2743-00-2 4-methoxy-N-(1-phenylethylidene)aniline 
• 92-91-1 biphenyl-4-acetaldehyde 
• 55190-50-6 4'-bromo-2'-phenyl-acetophenone 
• 2142-66-7 1-([1,1'-biphenyl]-2-yl)ethanone 
• 1439402-24-0 C₂₅H₂₈BrClIrNO 
• 1439402-24-0 C₂₅H₂₉BrClIrNO 
• 100865-02-9 5-methoxy-2-(4-bromophenyl)-1H-indole 

Relevant academic research and scientific papers

Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines

Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands.

Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control

An oxidative kinetic resolution of racemic acyclic amines was developed using an imine derivative as the resolving reagent and chiral phosphoric acid as the catalyst to give enantiomers in good yields with high to excellent enantioselectivities. The key t

HΒ Catalyzed Condensation Reaction Between Aromatic Ketones and Anilines: To Access Ketimines (Imines)

Abstract: A simple approach for the formation of imines by condensation of ketones and anilines over heterogeneous catalyst (Hβ zeolite) has been successfully developed. The present catalytic system scope was explored for various aromatic ketones and anil

Diverse reactivity of a tricoordinate organoboron L2PhB: (L = oxazol-2-ylidene) towards alkali metal, group 9 metal, and coinage metal precursors

The reactivity of a tricoordinate organoboron L2PhB: (L = oxazol-2-ylidene) 1 towards metal precursors and its coordination chemistry were comprehensively studied. While the boron center in 1 is reluctant to coordinate to the alkali metals in their trifluoromethanesulfonate salts (MOTf) (M = Li, Na, K), the unprecedented compound 2 containing two L2PhB: units linked by a cyclic Li(OTf)2Li spacer was obtained from the reaction of 1 with LiOTf. Treatment of 1 with group 9 metal complexes [MCl(COD)]2 (M = Rh, Ir) afforded the first zwitterionic rhodium(i)-boronium complex 3 and the iridium(iii)-borane complex 4, respectively. The reaction pathway may involve C-H activation followed by proton migration from the metals to the boron center, demonstrating the first example of the deprotonation of metal hydrides by a basic boron. In the reactions with coinage metals, 1 could act as a two-electron reducing agent towards the metal chlorides MCl (M = Cu, Ag, Au). Meanwhile, the reaction of 1 with gold chloride supported by a N-heterocyclic carbene (NHC) produced a heteroleptic cationic gold complex [(L2PhB)Au(NHC)]Cl (6) featuring both carbene and L2PhB: ligands on the gold atom. In contrast, an isolable gold chloride complex (L2PhB)AuCl (8) was obtained by direct complexation between 1 and triphenylphosphine-gold chloride via ligand exchange. X-ray diffraction analysis and computational studies revealed the nature of the B:→Au bonding interaction in complexes 6 and 8. Natural Population Analysis (NPA) and Natural Bond Orbital (NBO) analysis support the strong σ-donating property of the L2PhB: ligand. Moreover, preliminary studies showed that complex 8 can serve as an efficient precatalyst for the addition of X-H (X = N, O, C) to alkynes under ambient conditions, demonstrating the first application of a metal complex featuring a neutral boron-based ligand in catalysis.

Rh(III)-catalyzed synthesis of 1-substituted isoquinolinium salts via a C-H bond activation reaction of ketimines with alkynes

An efficient synthesis of highly substituted isoquinolinium salts from ketimines and alkynes via a Rh(III)-catalyzed C-H bond activation and annulation reaction is described. The Royal Society of Chemistry.

Pd(II)/Bu4NBr/DMSO catalytic system for practical synthesis of indoles and pyrroles from imines through aerobic dehydrogenative cyclization

N-Aryl- and N-allylimines derived typically from substituted acetophenones undergo palladium(II)-catalyzed dehydrogenative cyclization reactions in the presence of tetrabutylammonium bromide and molecular oxygen in DMSO to afford indole and pyrrole deriva

Highly efficient asymmetric-axle-supported N-O amides in enantioselective hydrosilylation of ketimines with trichlorosilane

A novel asymmetric-axle-supported chiral N-O amide was synthesized and used in catalytic enantioselective hydrosilylation of N-aryl ketimines with HSiCl3 at room temperature instead of the typical -20°C. High conversion yield and high enantiose

A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant

A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-l-proline anilide was carried out to give the co

Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: Indole synthesis from anilines and ketones

We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.

Highly enantioselective imine hydrogenation catalyzed by ruthenium phosphane-phosphite diamine complexes

Mildly does it: A highly enantioselective catalyst for the hydrogenation of N-aryl imines is described (see scheme). This catalyst offers practical advantages because it operates under very mild conditions and is based on an Ru complex with a diamine as t