Multi-step reaction with 4 steps
1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 °C / Inert atmosphere
1.2: 1.33 h / -78 °C / Inert atmosphere
2.1: zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex / tetrahydrofuran / 0.25 h / 25 °C / Inert atmosphere
2.2: 14 h / 45 °C / Inert atmosphere
3.1: palladium on carbon; ammonium formate / tetrahydrofuran; methanol / 0.5 h / 45 °C / Inert atmosphere
4.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; zinc(II) chloride / tetrahydrofuran / 1 h / 90 °C / Inert atmosphere; Microwave irradiation
4.2: 0 - 25 °C / Inert atmosphere
With
2,2,6,6-tetramethyl-piperidine; n-butyllithium; 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex; palladium on carbon; ammonium formate; zinc(II) chloride;
In
tetrahydrofuran; methanol; hexane;
2.2: Negishi coupling reaction;
DOI:10.1021/ol103057k