Mild and Regioselective Bromination of Aromatic Compounds withN,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide and Poly(N-bromobenzene-1,3-disulfonylamide)

Abstract

M i l d a n d R e g i o s e l e c t i v e B r o m i n a t i o n o f A r o m a t i c C o m p o u n d s

A New and Facile Protocol for the Synthesis of Dithiocarbamate-linked 3,4-Dihydro-2H-pyran Using N-Halo Catalysts Under Mild Conditions Reaction

“…In a continuation of our interest in the application of N,N,N',N'-tetrabromobenzene-1,3-disulfonamide (TBBDA) and poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) (PBBS), 22 (Scheme 1), in organic synthesis, [23][24][25][26][27][28][29][30][31][32][33][34][35] we wish to report here a facile and improved protocol for preparation of dithiocarbamate derivatives, from amines, carbon disulfide (CS 2 ) and 3,4-dihydro-2H-pyran in the presence of TBBDA and PBBS as catalysts in EtOH/H 2 O at ambient conditions (Scheme 1).…”

Efficient and solvent-free synthesis of 1-amidoalkyl-2-naphthols using N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide

“…IR spectra (KBr) were recorded on a Shimadzu Fx-90 infrared spectrophotometer and the nuclear magnetic resonance (NMR) spectra were obtained on a Jeol 90 MHz spectrometer using TMS as the internal standard. BNBTS was prepared according to our previously reported procedure [21].…”

“…Since TBBDA contains bromine atoms which are bonded to nitrogen atoms, it is possible that this catalyst releases Br + in situ, which can act as an electrophilic species [21][22][23][24][25][26]. Therefore, the following mechanism can be suggested for the synthesis of amidoalkyl naphthols (Scheme 2) [16][17][18][19].…”

“…In continuation of our interest in the application of N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] [21] (Fig. 1) in organic synthesis [22][23][24][25][26] we report here a convenient method of a one-pot synthesis of 1-amidoalkyl-2-naphthol derivatives from various aromatic aldehydes, β-naphthol, and urea, carried out with high yields in the presence of TBBDA, at room temperature, and under solvent-free conditions (Scheme 1).…”

Silica-supported quinolinium tribromide: a recoverable solid brominating reagent for regioselective monobromination of aromatic amines

“…or poly(N-bromobenzene-1,3-disulfonylamide), 13 1,2-dipyridiniumditribromide-ethane, 14 ethylenebis(Nmethylimidazolium) ditribromide, 15 1-butyl-3-methylpyridinium tribromide, 16 tert-butylhydroperoxide/ HBr, 17 LiBr/(NH 4 ) 2 Ce(NO 3 ) 6 , 18 KBr/NaBO 3 ·4H 2 O, 19 2 -m e t h y l -4 -p o l y ( s t y r y l m e t h y l ) t h i a z o l i u m hydrotribromide, 20 LiBr/(diacetoxyiodo)benzene, 21 alkalimetal bromide/NaIO 4 , 22 bromodimethylsulfonium bromide, 23 HBr/H 2 O 2 , 24 1,8-diazabicyclo [5.4.0]undec-7-ene hydrobromide perbromide, 25 metal bromides/ sodium bismuthate, 26 N-octyl quinolinium tribromide 27 and pyridinium hydrobromide perbromide. 28 However, some methods still suffer from drawbacks of difficult handling, low selectivity, low yield and corrosion.…”