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Cobalt(II)/TPPMS‐Catalyzed Dehydrative Nucleophilic Substitution of Alcohols in Water
Author(s) -
Hikawa Hidemasa,
Ijichi Yukiko,
Kikkawa Shoko,
Azumaya Isao
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601501
Subject(s) - chemistry , cobalt , amination , catalysis , allylic rearrangement , nucleophilic substitution , nucleophile , substitution reaction , sulfonate , lewis acids and bases , medicinal chemistry , organic chemistry , combinatorial chemistry , sodium
A green and sustainable direct dehydrative amination of alcohols, catalyzed by cobalt(II)/TPPMS (sodium diphenylphosphinobenzene‐3‐sulfonate) in water, is described. Earth‐abundant cobalt is used in form of Co(hfac) 2 · x H 2 O (hfac: hexafluoroacetylacetone), which acts as a highly efficient Lewis acidic catalyst. This simple atom‐economical protocol features mild conditions without the need for a base or other additives and affords the corresponding benzylic and allylic anilines along with water as the only coproduct. Mechanistic studies suggest that this system is driven by direct nucleophilic substitution of alcohols.