Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate

Abstract

A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.

Übergangsmetallfreie Synthese polyfunktioneller Triarylmethane und 1,1‐Diarylalkane durch sequentielle Kreuzkupplungen von Benzaldiacetaten mit Organozinkreagenzien

“…[2] Daher hat ihre Herstellung im Laufe des letzten Jahrzehnts viel Aufmerksamkeit auf sich gezogen. [3] Ty pischerweise werden Tr iarylmethane durch Friedel-Craftsartige Reaktionen (Schema 1a) [4,5] durch übergangsmetallkatalysierte Kreuzkupplungen hergestellt (Schema 1b). [6][7][8] Diese Methoden erwiesen sich auch nützlich fürdie Herstellung von ähnlichen 1,1-Diarylalkanen (Schema 1c).…”

TBAB-Catalyzed 1,6-Conjugate Sulfonylation of para-Quinone Methides: A Highly Efficient Approach to Unsymmetrical gem-Diarylmethyl Sulfones in Water

“…Among the sulfone family, diarylmethyl sulfones hold an essential position in biologically important compounds that show various biological activities, such as potassium channel inhibitory activity [8], as well as antidepressant [9] and anticancer properties (Figure 1) [10]. Additionally, diarylmethyl sulfones can be applied as useful intermediates for synthetic applications owing to the versatile reactivities of the sulfonyl group activated carbanions [1,[11][12][13][14]. Although a number of methodologies have been developed for the synthesis of diarylmethyl sulfones, most of the reported methods suffer from the harsh reaction conditions, multi-step procedures, Scheme 1.…”

Direct synthesis of completely unsymmetrical triarylmethanes via Fe(III) salt‐mediated in situ o‐quinone methides process

“…reaction in the presence of an acid catalyst, but poor regioselectivities were often obtained (Scheme 1a). [13][14][15][16][17][18][19][20][21][22][23][24] In recent years, a number of novel methods such as crosscoupling reactions [25][26][27][28][29][30] and C-H functionalization [31][32][33][34] have been developed. However, most of the reactions require expensive transition metals and ligands (Scheme 1b).…”

“…[ 10–12 ] The conventional method for the synthesis of unsymmetrical triarylmethanes is the Friedel–Crafts reaction in the presence of an acid catalyst, but poor regioselectivities were often obtained (Scheme 1a). [ 13–24 ] In recent years, a number of novel methods such as cross‐coupling reactions [ 25–30 ] and C–H functionalization [ 31–34 ] have been developed. However, most of the reactions require expensive transition metals and ligands (Scheme 1b).…”