An efficient and
novel photoinduced trifluoromethylation employing
CF
3
Br as a trifluoromethyl source is described. With commercially
accessible
fac
-Ir
(III)
(ppy)
3
as the catalyst, radical trifluoromethylation between
O
-silyl enol ether and CF
3
Br occurs successfully. This
method provides various α-CF
3
-substituted ketones
with a broad substrate scope in good yields under mild reaction conditions.
A novel and efficient method for synthesis of polysubstituted
trifluoromethylpyridine
derivatives by the Bohlmann–Rahtz heteroannulation reaction
is described, which use trifluoromethyl-α,β-ynones as
trifluoromethyl building blocks to react with β-enamino esters
or β-enamino ketones in the presence of ZnBr2 to
form the trifluoromethylpyridine derivatives in good yields. The protocol
has the advantages of readily available starting materials, mild reaction
conditions, and high atom economy.
An efficient cascade oxidation/halogenoaminocyclization reaction of homoallylhydrazides with N-halogensuccinimide was developed without addition of other additives under mild reaction conditions to provide pyrazolines. Under the optimized conditions, a variety of highly substituted pyrazoline derivatives were obtained. Keywords oxidation/halogenoaminocyclization; pyrazolines; homoallylhydrazides; N-halogensuccinimide 2 Results and discussion Based on our previous reaction conditions, [15] N'-(1phenylbut-3-en-1-yl)benzohydrazide (1a) was taken as substrate to react with NIS (2a) in tetrahedron (THF) at room temperature. After 4 h, N-benzoyl-5-iodomethyl-3phenylpyrazoline (3a) was obtained in 91% yield (Table 1). In order to investigate the generalities of the substrates,
Efficient visible-light-induced radical cascade trifluoromethylation/cyclization of inactivated alkenes with CF3Br, which is a nonhygroscopic, noncorrosive, cheap and industrially abundant chemical, was developed in this work, producing trifluoromethyl polycyclic quinazolinones, benzimidazoles and indoles under mild reaction conditions. The method features wide functional group compatibility and a broad substrate scope, offering a facile strategy to pharmaceutically produce valuable CF3-containing polycyclic aza-heterocycles.
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