7714-74-1

Upstream product

• 74-87-3 methylene chloride 
• 574-45-8 N-(diphenylmethylidene)phenylamine 
• 108-86-1 bromobenzene 
• 4960-31-0 Tris(methylphenylamino)methan 
• 91-01-0 1,1-Diphenylmethanol 
• 100-61-8 N-methylaniline 
• 908093-98-1 diazodiphenylmethane 
• 5350-57-2 benzophenone hydrazone 
• 119-61-9 benzophenone 
• 781-35-1 1,1-diphenylacetone 
• 103-79-7 1-phenyl-acetone 

Relevant academic research and scientific papers

Silver-Catalyzed N-H Functionalization of Aryl/Aryl Diazoalkanes with Anilines

Herein, we report on the N-H functionalization reaction of primary and secondary anilines with diaryldiazoalkanes using simple AgPF6 as catalyst. We demonstrated broad applicability in the reaction of diaryldiazoalkanes with different anilines (31 examples, up to 97% yield). Furthermore, we propose a possible reaction mechanism for the N-H functionalization.

Benzyl C–O and C–N Bond Construction via C–C Bond Dissociation of Oxime Ester under Visible Light Irradiation

A photoredox benzyl activation was developed via formidable C(sp3)–C(sp3) bond dissociation of 1-aryl acetone oxime esters, which were easily prepared from benzyl ketones. Further coupling with O- and N- nucleophiles successfully forged important benzyl ether and amines derivatives in one pot. In this process, different substitutions on oxime esters were found compatible and various primary and secondary alcohols and amines, as well as amides showed good performance as nucleophiles. Mechanistic studies by control experiments, electrochemical measurements and in-situ NMR spectra proposed a N–O bond interruption/C–C bond fragmentation/oxidation sequence to provide the key cation intermediate for the next electrophilic SN process. The features of mild condition, short reaction time and broad substrate scope made this new strategy much promising in the transformation of benzyl compounds, which might be valuable in last-stage functionalizations.

Boron-Catalyzed N-Alkylation of Arylamines and Arylamides with Benzylic Alcohols

A sustainable boron-based catalytic approach for chemoselective N-alkylation of primary and secondary aromatic amines and amides with primary, secondary, and tertiary benzylic alcohols has been presented. The metal-free protocol operates at low catalyst loading, tolerates several functional groups, and generates H2O as the sole byproduct. Preliminary mechanistic studies were performed to demonstrate the crucial role of boron catalyst for the activation of the intermediate dibenzyl ether and to identify the rate-determining step.

Ligand-free Iron(II)-Catalyzed N-Alkylation of Hindered Secondary Arylamines with Non-activated Secondary and Primary Alcohols via a Carbocationic Pathway

Secondary benzylic alcohols represent a challenging class of substrates for N-alkylation of amines. Herein, we describe an iron(II)-catalyzed eco-friendly protocol for N-alkylation of secondary arylamines with secondary benzyl alcohols through a carbocationic pathway instead of the known borrowing hydrogen transfer (BHT) approach. Transiently generated carbocations, produced from alcohols via self-condensation, were coupled with arylamines to provide highly functionalized amine products. The scope of this methodology involves N-alkylation of primary, secondary and heterocyclic amines with primary/secondary benzylic, allylic and heterocyclic alcohols, which are common key structures in numerous pharmaceuticals drugs. The method can also be easily adopted for the amination of various natural products. (Figure presented.).

Extremely Reactive C=C Double Bonds, VI. - Tris(methylphenylamino)methane - The Chemistry of Orthoamides

Reactions of the title compound 2 with sulfur, selenium, thiophenol, malononitrile, 1,3-indanedione, fluorenone hydrazone, phenylmagnesium bromide, bromine, thioacetic acid, N,N'-diphenylurea, oxalyl chloride, 9,9-dichloroxanthene, phenyl isocyanate, and stilbene dibromide are described and the mechanisms are discussed.The catalytic influence of 2 on the decomposition of 9-diazofluorene in xylene and mesitylene is discussed.