TY - JOUR
T1 - Partially fluorinated heterocycles from 4,4-bis(trifluoromethyl)-hetero-1, 3-dienes via C-F bond activation - Synthesis of 2-fluoro-3-(trifluoromethyl) furans
AU - Burger, Klaus
AU - Helmreich, Brigitte
AU - Hennig, Lothar
AU - Spengler, Jan
AU - Albericio, Fernando
AU - Fuchs, Annett
PY - 2007/3
Y1 - 2007/3
N2 - An efficient synthesis of 2-fluoro-3-(trifluoromethyl)furans was developed. Keystep of the reaction sequence is a [4 + 1] cycloaddition reaction of tin(II)chloride to 4,4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes. At elevated temperatures the tin heterocycles are transformed into 1-aryl-4,4-difluoro-3- (trifluoromethyl)but-3-en-1-ones which on treatment with sodium hydride in dry DMF give 2-fluoro-3-(trifluoromethyl)furans. The single fluorine bound to C-(2) can be readily replaced by various N-, O-, S-, and C-nucleophiles and dinucleophiles.
AB - An efficient synthesis of 2-fluoro-3-(trifluoromethyl)furans was developed. Keystep of the reaction sequence is a [4 + 1] cycloaddition reaction of tin(II)chloride to 4,4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes. At elevated temperatures the tin heterocycles are transformed into 1-aryl-4,4-difluoro-3- (trifluoromethyl)but-3-en-1-ones which on treatment with sodium hydride in dry DMF give 2-fluoro-3-(trifluoromethyl)furans. The single fluorine bound to C-(2) can be readily replaced by various N-, O-, S-, and C-nucleophiles and dinucleophiles.
KW - 1-Aryl-4,4-difluoro-3- (trifluoromethyl)but-3-en-1-ones
KW - 3-(Trifluoromethyl)tetrahydrocumaron
KW - [4 + 1] Cycloaddition
KW - Bridged 3-(trifluoromethyl)furans
KW - C-F Bond activation
UR - https://www.scopus.com/pages/publications/33847783306
U2 - 10.1007/s00706-007-0587-4
DO - 10.1007/s00706-007-0587-4
M3 - Artículo
AN - SCOPUS:33847783306
SN - 0026-9247
VL - 138
SP - 227
EP - 236
JO - Monatshefte fur Chemie
JF - Monatshefte fur Chemie
IS - 3
ER -