Dehydrative Thiolation of Allenols: Indium vs Gold Catalysis
摘要:
Intermolecular additions of thiols to allenols via formal S(N)2' selectivity to produce functionalized dienes are described. Although this dehydrative reaction was initially developed using gold(I) catalysis, indium(III) proves to be a far superior catalyst in terms of selectivity and substrate scope.
Electrophilic Cyclizations of Diaryl-2,3-allenyl Ethers with <i>N</i>-Bromosuccinimide: En Route to 2-Bromonaphthalenes
作者:Minyan Wang、Jing Li、Chunling Fu、Shengming Ma
DOI:10.1021/ol502100k
日期:2014.10.3
The reaction of diaryl-2,3-allenyl ethers with N-bromosuccinimide in a mixed solvent of CH3NO2/EtOH affords highly functionalized 2-bromonaphthalenes in 21-66% yields. The electronic effect on the aryl is important to the selectivity of the reaction; when 4-(trifluoromethyl)phenyl or 1 naphthyl was applied as one of the two aryl groups, the regioselectivity was practical, affording the products with the other relatively electron-rich phenyl ring or the non-1-napthyl group being cyclized as the major, respectively.