A Novel Regiospecific Synthesis of 1-Chloro-2-arylcyclohexenes

Table 1

Suzuki cross coupling of 2 with 3a using different palladium catalysts/solvents.

Entry	Catalyst	Base	Ligand	Solvent	% Yield
01	Pd(OAc)2	K2CO3	PPh3	Ethanol	40	—
02	Pd(OAc)2	K2CO3	P(t-Bu)3	Ethanol	25	—
03	Pd(OAc)2	TEA	P(o-tol)3	Ethanol	30	—
04	(PPh3)2PdCl2	K2CO3	PPh3	Toluene	35	5
05	(PPh3)2PdCl2	K2CO3	P(o-tol)3	Ethanol	25	10
06	(PPh3)2PdCl2	Cs2CO3	P(t-Bu)3	Toluene	30	15
07	Pd(PPh3)2Cl2	TEA	P(o-tol)3	Dioxane	35	30
08	Pd(PPh3)4	Cs2CO3	—	Dioxane	20	45
09	Pd(dppf)Cl2·CH2Cl2^∗	K2CO3	—	Dioxane	20	60
					<5	>90

∗Reactions were carried out both at reflux condition and in sealed tube.