96328-02-8

Upstream product

• 127-19-5 N,N-dimethyl acetamide 
• 100-52-7 benzaldehyde 
• 23184-28-3 N,N-dimethyl(trimethylsilyl)acetamide 
• 18871-71-1 N,N-dimethyl 3-oxo-3-phenyl-propanamide 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 98-86-2 acetophenone 
• 1191104-08-1 N,N-dimethyl-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide 
• 5908-41-8 benzoyltrimethylsilane 

Downstream Products

• 86-21-5 pheniramine 
• 26218-50-8 N,N-dimethyl-3-phenylpropiolamide 
• 76929-37-8 N,N-dimethyl-3-oxo-3-phenylpropanethioamide 
• 18871-71-1 N,N-dimethyl 3-oxo-3-phenyl-propanamide 
• 1354724-78-9 (R)-(2-(dimethylamino)-5-(1-hydroxyheptyl)thiophen-3-yl)(phenyl)methanone 
• 1354724-77-8 (R)-N-(1-(4-benzoyl-5-(dimethylamino)thiophen-2-yl)heptyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

N-heterocyclic carbene mediated Reformatsky reaction of aldehydes with a-trimethylsilylcarbonyl compounds

N-Heterocyclic carbenes have been employed as highly efficient organocatalysts to mediate silyl-Reformatsky type reaction. In the presence of only 0.5 mol % nucleophilic carbene 1, various aldehydes coupled with α-trimethylsilylethylacetate very smoothly in DMF at room temperature to provide the corresponding β-hydroxyesters in moderate to high yields. α-Trimethylsilylketone and α-trimethylsilylamide can also undergo the addition reaction to give β-hydroxyketone and b-hydroxyamide in moderate yields.

Optically active thiophenes via an organocatalytic one-pot methodology

A general methodology for the synthesis of trisubstituted, optically active thiophenes by an organocatalytic one-pot reaction cascade is presented. The target products are synthesized in good yields (up to 92%) and with excellent enantioselectivities (up to 98% ee). Importantly, based on practical and easily available starting materials, the presented methodology can be conducted under mild reaction conditions. To further elucidate the generality, the synthesis of optically active thienoindoles, as well as selenophenes, is also demonstrated.

Isoquinoline-based chiral monodentate N-heterocyclic carbenes

C1-symmetric isoquinoline-based chiral diaminocarbene ligands (MIQ) have been developed to block three quadrants of the metal coordination sphere, complementing C2-symmetric biisoquinoline-based ligands (BIQ). MIQ-Cu complexes catalyzed conjugate borylation of various α,β-unsaturated amides in good yields (82-99%) and enantioselectivities (75-87% ee).

Amide enolate additions to acylsilanes: In situ generation of unusual and stereoselective homoenolate equivalents

The synthesis of β-hydroxy carbonyl compounds is an important goal due to their prevalence in bioactive molecules. A novel approach to construct these structural motifs involves the multicomponent reaction of acylsilanes, amides, and electrophiles. The ad

Synthesis of tertiary β-hydroxy amides by enolate additions to acylsilanes

The synthesis of tertiary β-hydroxy amides from acylsilanes, acetamides, and electrophiles is described. The addition of amide enolates to acylsilanes generates β-silyloxy homoenolate reactivity by undergoing a 1,2-Brook rearrangement. These unique nucleo

Cerium(III) amide enolate. Addition to aldehydes and ketones

The cerium(III) amide enolates, prepared in situ from the corresponding lithium enolates and anhydrous CeCl3, were found to undergo facile additions to ketones and aldehydes. Yields of the adducts are superior to those obtained using the lithiu

ADDITION OF STANNYLATED CARBOXYLIC ACID DERIVATIVES TO THE CARBONYL GROUP OF ALDEHYDES

Addition reactions of Bu3SnCH2COOEt with PhCHO at 75 deg C in the presence of Bu3SnI and reactions of Et3SnCH2X (X=COOEt, CN, CONMe2) with benzaldehyde, cynnamaldehyde and furfural at 20 deg C in DMSO in the presence of Me4NF (2 mol percent) were investigated.Adducts obtained in high yield in these reactions readily undergo hydrolysis (when treated with aqueous KF) and acetolysis (when treated with AcCl) with quantitative formation of 3-hydroxy and 3-acetoxy derivatives of esters, nitriles and amides.We show that interaction of Et3SnCH2COOEt with the above-mentioned aldehydes and isovaleraldehyde in the presence of equimolar amounts of Et4NCl in CH2Cl2/HMPTA (10/1) at 20 deg C followed by treatment of the reaction mixture with AcCl readily gives 3-acetoxyesters.Reactions of PhCH(SnMe3)COOEt with acrolein, crotonaldehyde and cinnamaldehyde and the hydrolysis of the obtained adducts lead exclusively to 1,2-addition products, these reactions are virtually non-stereoselective.The reaction of PhCH(SnMe3)COOEt with benzaldehyde at 20 deg C in DMF, CH2Cl2 or without solvent gives mainly threo-ethyl(2,3-diphenyl-3-hydroxy)propoinate whereas at -78 deg C in CH2Cl2 in the presence of BF3*Et2O erythro isomer is mainly formed.The data obtained are discussed within the framework of the mechanism involving the participation of the O-isomer CH2=C(OEt)OSnR3.This active intermediate is formed via metallotropic rearrangement of the starting organotin compound.