TY - JOUR
AU1 - Burger, Klaus
AU2 - Helmreich, Brigitte
AU3 - Hennig, Lothar
AU4 - Spengler, Jan
AU5 - Albericio, Fernando
AU6 - Fuchs, Annett
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.
TI - Partially Fluorinated Heterocycles from 4,4-Bis(trifluoromethyl)-hetero-1,3-dienes via C–F Bond Activation – Synthesis of 2-Fluoro-3-(trifluoromethyl)furans
JF - Monatshefte für Chemie - Chemical Monthly
DO - 10.1007/s00706-007-0587-4
DA - 2007-02-23
UR - https://www.deepdyve.com/lp/springer-journals/partially-fluorinated-heterocycles-from-4-4-bis-trifluoromethyl-hetero-AA2zrlb7Ib
SP - 227
EP - 236
VL - 138
IS - 3
DP - DeepDyve
ER -