1,6-Conjugate sulfonylation of para-quinone methides: An expedient approach to unsymmetrical gem-diarylmethyl sulfones

The crystal structure of 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S

“…In addition, diarylmethylamines are also widely used as important synthetic intermediates in medicinal chemistry and materials science [8][9][10]. Our group has maintained a keen interest in the synthesis of the sulfones [11,12] and diarymethyl derivatives [13]. We first synthesized the 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol and obtained the crystal of it.…”

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

“…The reaction between p ‐quinone methides 337 and sulfonyl hydrazides 338 [182] or sodium sulfinates 339 [183] resulted in substituted 4‐(sulfonylmethyl)phenols 340 in high yields (Scheme 147). Similar products were also prepared by three‐component reaction of aldehydes, sodium sulfinates, and di‐ or trimethoxybenzenes in the presence of Amberlyst‐15 in water [184] …”

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

“…Unfortunately, heterogeneous transition metal nano-catalysts such as Pd/C, Pd/TiO2, Au/TiO2, and Pt/C had little promotion effect on the reaction (Table 1, entry 9-12). Inspired by the better result of EtOH, phase transfer catalysts were selected to improve the solubility of organic substrate 1a and 2a in water, which may have a positive influence on the reaction (Table 1, entry [13][14][15][16][17]. To our delight, in presence of 10% mol tetrabutylammonium bromide (TBAB), the yield was improved sharply to 82% (Table 1, entry 16).…”

“…Di-tert-butyl-4-(phenyl(tosyl)methyl)phenol (3aa):[15] Pale yellow solid; 96% yield.1 H-NMR (600 MHz, CDCl 3 ) δ 7.61 (d, J = 7.1 Hz, 2H), 7.42 (d, J = 8.0 Hz, 2H), 7.32 (dq, J = 14.2, 6.9 Hz, 3H), 7.16 (s, 2H), 7.13 (d, J = 7.9 Hz, 2H), 5.20 (s, 1H), 5.16 (s, 1H), 2.36 (s, 3H), 1.35 (s, 18H); 13 C-NMR (151 MHz, CDCl 3 ) δ 154.08 (s), 144.00 (s), 135.94 (s), 135.77 (s), 133.66 (s), 130.00 (s), 129.10 (s), 129.05 (s), 128.62 (s), 128.36 (s), 127.10 (s), 123.57 (s), 76.90 (s), 34.31 (s), 30.16 (s), 21.48 (s). 2,6-Di-tert-butyl-4-(o-tolyl(tosyl)methyl)phenol (3ab): [15] Pale yellow solid; 76% yield.…”