Palladium-mediated synthesis of 1,1,2-triarylethanes. Application to the synthesis of CDP-840

Hydrogenation of β-Keto Sulfones to β-Hydroxy Sulfones with Alkyl Aluminum Compounds: Structure of Intermediate Hydroalumination Products

“…The results of the conversion of β-keto sulfones to β-hydroxy sulfones are presented in Table 1 . Mp of 2-hydroxy-2-phenyethyl-4-mehylphenylsulfone 4a : 74–75 °C, (literature data 69–71 °C [ 17 ], 69.4–70.8 °C [ 51 ], 78–79 °C [ 52 ] and 74–75 °C [ 53 ]; Mp of 2-hydroxy-2-phenyethyl-4-chlorophenylsulfone 4b : 105–107 °C (literature data 106–108 °C [ 53 ], 105–106 °C [ 54 ] and 103.5–105 °C [ 55 ]); Mp of 1-(4-methylphenylsulfonyl)propan-2-ol 4c : 75–76 °C (literature data 78 °C [ 56 ]); Mp of 2-[(4’-methylphenyl)sulfonyl]-1,2-diphenylethanol 4d : 159–160 °C (literature data 156–157 °C [ 57 ]) and Mp of 1-phenyl-2-(4-methylphenylsulfonyl)propan-1-ol 4e : 100–103 °C (literature data 99–100.5 °C [ 58 ]).…”

“…However, the reduction of carbonyl group of β-keto sulfones is considered as the most popular method of β-hydroxy sulfones synthesis. The reduction with NaBH 4 without the addition of chiral additives leads to a racemic mixture of β-hydroxy sulfones [ 17 , 18 , 19 , 20 ], while enzymatic reduction and chemical enantioselective reduction of the C=O group lead to the chiral β-hydroxy sulfones with high enantioselectivity [ 21 , 22 , 23 , 24 , 25 ].…”

Beyond classical sulfone chemistry: metal- and photocatalytic approaches for C–S bond functionalization of sulfones

“…151,152 The first example of this chemistry using alkyl sulfones was reported by Kuei, Chang and co-workers in the context of the Pd-catalysed desulfonylative arylation (Scheme 78a). 153 The authors found that the treatment of primary alkyl methyl sulfones reacted with different aryl iodides in the presence of catalytic amounts of Pd(OAc) 2 in combination with KO t Bu. Interestingly, the catalytic system was able to differentiate the two different C(sp 3 )–S bonds with the exclusive functionalization of the larger, substituted alkyl group.…”

“…151,152 The first example of this chemistry using alkyl sulfones was reported by Kuei, Chang and co-workers in the context of the Pd-catalysed desulfonylative arylation (Scheme 78a). 153 The authors found that the treatment of primary alkyl methyl sulfones reacted with different aryl iodides in the presence of catalytic Scheme 76 a-Fluoroalkylaryl trifluoromethyl sulfones as electrophiles.…”

“…Thus, challenges regarding the possibility of non-desired outcomes and/or lack of reactivity need to be avoided 151,152. The first example of this chemistry using alkyl sulfones was reported by Kuei, Chang and co-workers in the context of the Pd-catalysed desulfonylative arylation (Scheme 78a) 153. The authors found that the treatment of primary alkyl methyl sulfones reacted with different aryl iodides in the presence of catalytic Scheme 76 a-Fluoroalkylaryl trifluoromethyl sulfones as electrophiles.Scheme 77 Construction of all-carbon quaternary stereocenters via Nicatalysed Suzuki Miyaura with benzylic sulphones as electrophiles.Scheme 78 Alkyl sulfones in reductive cross-coupling chemistry.…”