EP 1115679 A1 20010718 - METHOD FOR PRODUCING OLEFINS
Title (en)
METHOD FOR PRODUCING OLEFINS
Title (de)
VERFAHREN ZUR HERSTELLUNG VON OLEFINEN
Title (fr)
PROCEDE DE PRODUCTION D'OLEFINES
Publication
Application
Priority
- DE 19843012 A 19980921
- EP 9906589 W 19990907
Abstract (en)
[origin: DE19843012A1] In the preparation of (hetero)aryl-substituted olefins (I) by palladium-catalyzed reaction of a (hetero)aromatic halide, sulfonate or diazonium halide (II) with an olefin (III), the catalyst is a specific divalent palladium compound (IV) used in presence of a nitrogen-containing additive (V), and reaction is in the absence of phosphonium salts and phosphanes. Preparation of (hetero)aryl-substituted olefins of formula Ar-C(R1)=CR2R3 (I) involves palladium-catalyzed reaction of a (hetero)aromatic compound of formula ArZ (II) with an olefin of formula HC(R1)=CR2R3 (III). The catalyst is a divalent palladium compound of formula PdXY (IV) (or its acetonitrile of benzonitrile complex) used in presence of a nitrogen-containing additive (V). Reaction is carried out at 60-180 deg C, in the presence of a solvent and a base, but in the absence of phosphonium salts and phosphanes. Ar = aryl or heteroaryl (both optionally substituted); R1-R3 = H, 1-8C alkyl, Ph, 1- or 2-naphthyl, 1-8C alkoxy, OPh, CN, COOH,(1-8C) alkoxycarbonyl, COOPh, CONH2, N-(1-5C alkyl)-amido, N,N-di-(1-5C alkyl)-amido, F, Cl, PO(Ph)2, PO(1-5C alkyl)2, Ph-CO, 1-5C alkyl-CO, 1-4C alkylamino, PO3H (sic), 1-4C alkylsulfonate or 1-4C alkylsulfonyl; or R1 + R2 or R2 + R3 = (CH2)n; n = 2-12; Z = Cl, Br, OSO2Me, OS2-tolyl, OSO2CF3, OS2C4F9 or N2<+>.Cl<->; X, Y = Cl, Br, I, NO3, RCOO or R'SO3; R = 1-22C group, CF3, CCl3, CH2OMe or Ph; R' = 1-22C group, CF3, C4F9, CCl3, Ph or p-tolyl.
IPC 1-7
IPC 8 full level
C07B 37/04 (2006.01); C07B 61/00 (2006.01); C07C 2/86 (2006.01); C07C 15/52 (2006.01); C07C 17/266 (2006.01); C07C 22/08 (2006.01); C07C 41/30 (2006.01); C07C 43/215 (2006.01); C07C 45/68 (2006.01); C07C 49/796 (2006.01); C07C 67/343 (2006.01); C07C 69/618 (2006.01); C07C 201/12 (2006.01); C07C 205/06 (2006.01); C07C 209/68 (2006.01); C07C 209/74 (2006.01); C07C 211/48 (2006.01); C07C 253/30 (2006.01); C07C 255/50 (2006.01); C07C 211/45 (2006.01)
CPC (source: EP US)
C07B 37/04 (2013.01 - EP US); C07C 2/861 (2013.01 - EP US); C07C 17/266 (2013.01 - EP US); C07C 41/30 (2013.01 - EP US); C07C 45/68 (2013.01 - EP US); C07C 67/343 (2013.01 - EP US); C07C 201/12 (2013.01 - EP US); C07C 209/68 (2013.01 - EP US); C07C 253/30 (2013.01 - EP US); C07C 2531/22 (2013.01 - EP US)
Citation (search report)
See references of WO 0017132A1
Designated contracting state (EPC)
AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE
DOCDB simple family (publication)
DE 19843012 A1 20000323; CA 2345017 A1 20000330; EP 1115679 A1 20010718; JP 2002526460 A 20020820; US 6392111 B1 20020521; WO 0017132 A1 20000330
DOCDB simple family (application)
DE 19843012 A 19980921; CA 2345017 A 19990907; EP 9906589 W 19990907; EP 99969404 A 19990907; JP 2000574047 A 19990907; US 78778601 A 20010321