2,6-di-tert-butyl-4-methyl-phenol; N-ethyl-N,N-diisopropylamine; bis(benzonitrile)palladium(II) dichloride in tetrahydrofuran; N,N-dimethyl-formamide T=20°C; Stille cross-coupling; 16 h;

1: (2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol With tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; Hiyama Coupling; 0.5 h; Inert atmosphereDarkness; 2: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex in tetrahydrofuran Hiyama Coupling; 1 h; Inert atmosphereDarkness;

tetrakis(triphenylphosphine) palladium(0); TlOH in tetrahydrofuran 0.5 h; Ambient temperature;

pyrrolidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in tetrahydrofuran Sonogashira Cross-Coupling; 6 h; Inert atmosphereDarkness;

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; pyrrolidine / tetrahydrofuran / 6 h / |Inert atmosphere; |Darkness 2: [RhCl(η2:η2-cycloocta-1,5-diene)]2 / dichloromethane / 6 h / 20 °C / |Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4: manganese(IV) oxide; sodium carbonate / dichloromethane / 4 h / |Inert atmosphere View Scheme

tris(dibenzylideneacetone)dipalladium (0); triphenyl-arsane in various solvent(s) T=60°C; Alkylation; 3 h;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '4659073', constants.ctx, '0')">1-(2',6',6'-Trimethylcyclohex-1'-enyl)-but-1-ene-3-yne</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '16895481', constants.ctx, '0')">methylmagnesium tributylstannane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br /> <br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '969135', constants.ctx, '0')">methyl iodide</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br /> <br />Stage #3: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587194', constants.ctx, '0')">iodine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br /> <br /> &nbsp;

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '13197608', constants.ctx, '0')">zirconocene dichloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605264', constants.ctx, '0')">1,2-dichloro-ethane</a> <br />Negishi's method;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587194', constants.ctx, '0')">iodine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605264', constants.ctx, '0')">1,2-dichloro-ethane</a> <br /> <br /> &nbsp;

&nbsp;Yield given. Multistep reaction;&nbsp;<br /> &nbsp;