- A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines
-
The addition of InBr3 to the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane led to a dramatic increase in the reactivity to afford the corresponding 1,3-enynes bearing a trifluoromethyl group on their terminal sp2 carbon. The subsequent cyclization of these 1,3-enynes under palladium catalysis provides access to the corresponding indoles bearing a 3,3,3-trifluoroprop-1-enyl group at their 2-position.
- Ikeda,Omote,Kusumoto,Komori,Tarui,Sato,Ando
-
supporting information
p. 2127 - 2133
(2016/02/18)
-
- Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene
-
Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.
- Shen, Hao,Vollhardt, K. Peter C.
-
supporting information; experimental part
p. 208 - 214
(2012/03/11)
-
- Synthesis of pyrrolnitrin and related halogenated phenylpyrroles
-
A general approach to halogenated arylpyrroles, including the antifungal natural product pyrrolnitrin, is described using newly synthesized halogenated pyrroles and 2,6-disubstituted nitrobenzenes or 2,6-disubstituted anilines.
- Morrison, Matthew D.,Hanthorn, Jason J.,Pratt, Derek A.
-
supporting information; experimental part
p. 1051 - 1054
(2009/07/18)
-
- Mild and regioselective oxidative bromination of anilines using potassium bromide and sodium perborate
-
The selective monobromination of various deactivated anilines using potassium bromide and sodium perborate as oxidant has been achieved. The use of ammonium molybdate as catalyst accelerates the rate of reaction but is not essential to obtain good yields and high selectivities. (C) 2000 Elsevier Science Ltd.
- Roche, Didier,Prasad, Kapa,Repic, Oljan,Blacklock, Thomas J.
-
p. 2083 - 2085
(2007/10/03)
-
