caesium carbonate; tris(dibenzylideneacetone)dipalladium (0); 1,3-bis(2,6-diisopropylphenyl)imidazolinium in dimethyl amine T=140°C; intramolecular Heck reaction; Title compound not separated from byproducts;

potassium tert-butylate in dimethyl sulfoxide T=0 - 25°C;

1: LDA / tetrahydrofuran / -78 °C 2: Cs2CO3 / Pd2(dba)3; 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazolium / dimethylamine / 140 °C View Scheme

1: LDA / tetrahydrofuran / -78 °C 2: Cs2CO3 / Pd2(dba)3; 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazolium / dimethylamine / 140 °C View Scheme

1: LDA / tetrahydrofuran / -78 °C 2: Cs2CO3 / Pd2(dba)3; 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazolium / dimethylamine / 140 °C View Scheme

1: boron trifluoride diethyl etherate / anhydrous xylene / 135 - 140 °C / Inert atmosphere 2: Grubb's 2nd generation catalyst; toluene-4-sulfonic acid / dichloromethane / 24 h / 20 °C / Inert atmosphere 3: potassium tert-butylate / dimethyl sulfoxide / 0 - 25 °C View Scheme

1: Grubb's 2nd generation catalyst; toluene-4-sulfonic acid / dichloromethane / 24 h / 20 °C / Inert atmosphere 2: potassium tert-butylate / dimethyl sulfoxide / 0 - 25 °C View Scheme

1: sodium hydride / N,N-dimethyl-formamide / 0 - 25 °C 2: boron trifluoride diethyl etherate / anhydrous xylene / 135 - 140 °C / Inert atmosphere 3: Grubb's 2nd generation catalyst; toluene-4-sulfonic acid / dichloromethane / 24 h / 20 °C / Inert atmosphere 4: potassium tert-butylate / dimethyl sulfoxide / 0 - 25 °C View Scheme