712302-46-0Relevant academic research and scientific papers
Direct Use of Benzylic Alcohols for Gold(III)-Catalyzed S-Benzylation of Mercaptobenzoic Acids in Water
Hikawa, Hidemasa,Tada, Ayaka,Kikkawa, Shoko,Azumaya, Isao
supporting information, p. 395 - 402 (2016/02/12)
We demonstrate the gold(III)-catalyzed direct substitution of benzylic alcohols in water. These atom economic and environmentally benign protocols afford S-benzylated products in moderate to excellent yields. In contrast, common Lewis or Br?nsted acids as
Cationic palladium(II)-catalyzed dehydrative nucleophilic substitutions of benzhydryl alcohols with electron-deficient benzenethiols in water
Hikawa, Hidemasa,Machino, Yumo,Toyomoto, Mariko,Kikkawa, Shoko,Azumaya, Isao
, p. 7038 - 7045 (2016/07/30)
An efficient direct nucleophilic substitution of benzhydryl alcohols with electron-deficient benzenethiols using cationic Pd(ii) catalysts as Lewis acids in water is reported. Atom economical and environmentally benign protocols afford S-benzylated produc
A Radical Pathway for Direct Substitution of Benzyl Alcohols with Water-Soluble Copper Catalyst in Water
Hikawa, Hidemasa,Mori, Yuki,Kikkawa, Shoko,Azumaya, Isao
, p. 765 - 773 (2016/03/09)
We have developed a novel strategy for the direct substitution of benzyl alcohols with anthranilic acids using water-soluble copper catalysts through a radical pathway in water, which offers efficient and environmentally friendly N-, S-, and C-benzylations under neutral conditions. Radical scavengers strongly inhibited the benzylation. Radical clock experiments using α-cyclopropylbenzyl alcohol were conducted to observe the rapid isomerization of the cyclopropylmethyl radical to the allylmethyl radical. Hammett plots could be fitted to a two-parameter Hammett relationship containing both radical and polar contributions [log (kX/kH)=-1.24 σ.-0.38 σ, R2=0.99]. The relative parameter ρ./ρ of 3.3 suggested that these reactions involved a strong radical character with minor polar influence at the transition state.
Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via (η3-benzyl)palladium(II) cations in water
Hikawa, Hidemasa,Azumaya, Isao
, p. 5964 - 5972 (2014/08/05)
Mercaptobenzoic acid-palladium(0) complexes show high catalytic activity for S-benzylation with benzylic alcohols via the (η3-benzyl) palladium(ii) cation in water. Notably, these palladium(0) complexes could play an important role in formation
