71572-22-0

Upstream product

• 76709-17-6 C₈H₂₁NO₂Si₂ 
• 98-88-4 benzoyl chloride 
• 18166-02-4 N-trimethylsilylmethylamine 
• 4206-67-1 iodo(trimethylsilyl)methane 
• 55-21-0 benzamide 
• 445-29-4 o-fluoro-benzoic acid 
• 75-77-4 chloro-trimethyl-silane 
• 52833-63-3 2‐fluoro‐N‐methylbenzamide 
• 393-52-2 2-Fluorobenzoyl chloride 

Downstream Products

• 101402-29-3 N-<(trimethylsilyl)methyl>thiobenzamide 
• 1066-40-6 Trimethylsilanol 
• 101402-37-3 (3R,4R)-5-Phenyl-3,4-dihydro-2H-pyrrole-3,4-dicarboxylic acid dimethyl ester 
• 82959-86-2 2-methyl-4-phenyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione 
• 82959-86-2 2-methyl-4-phenyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione 
• 82959-87-3 methyl 2-phenylpyrrolidine-3-carboxylate 
• 82959-87-3 cis-3-(methoxycarbonyl)-2-phenylpyrrolidine 

Relevant academic research and scientific papers

Site-Selective Silylation of Aliphatic C-H Bonds Mediated by [1,5]-Hydrogen Transfer: Synthesis of α-Sila Benzamides

The first example of site-selective silylation of C(sp3)-H bonds mediated by a [1,5]-hydrogen transfer is reported. This reaction occurs selectively at the α-position of benzamides with a combination of tert-butylmagnesium chloride and a catalytic amount of 4,4′-di-tert-butylbipyridine (dtbpy) ligand and provides a facile route for the creation of biologically interesting α-sila benzamides. Late-stage functionalization of the incorporated silyl moieties facilitates the synthesis of N-formyl, cis-enamine, β-hydroxyl, amino, and pyrrole-containing derivatives.

One-Pot Reductive 1,3-Dipolar Cycloaddition of Secondary Amides: A Two-Step Transformation of Primary Amides

The one-pot reductive 1,3-dipolar cycloaddition of secondary aromatic N-(trimethylsilylmethyl)amides with reactive dipolarophiles is reported. The method relies on the in situ generation of nonstabilized NH azomethine ylide dipoles via amide activation with triflic anhydride, partial reduction with 1,1,3,3-tetramethyldisiloxane (TMDS), and desilylation with cesium fluoride (CsF). Running under mild conditions, the reaction tolerated several sensitive functional groups and provided cycloadducts in 71-93% yields. The use of less reactive dipolarophile methyl acrylate led to the cycloadduct in only 40% yield. A (Z) geometric intermediate of NH-azomethine 1,3-dipole was postulated to account for the observed higher yields and higher cis diastereoselectivity for the substrates bearing an electron-withdrawing group. This model features an unconventional cyclic transition state via carbanion-aryl ring interaction. Because the starting secondary amides can be prepared from common primary amides, the current method also constitutes a two-step transformation of primary amides.