Highly Stereoselective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions

Scott E. Denmark, Zhigang Wang

Organic Letters · 2001 · 10.1021/ol0156751

★ 3.0 1 rating

5 : Major extension (new functional group) –

4 : Minor extension (no new functional group) –

3 : Reproduced as published ×1

2 : Reproduced with deviation –

1 : Did not work –

– : Extension failed / Inconclusive –

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16 Jul 2026

★ 3 : Reproduced as published

Sourced from Org. Synth. "Platinum catalyzed hydrosilylation and palladium catalyzed cross-coupling: One-pot hydroarylation of 1-heptyne to (E)-1-(1-heptenyl)-4-methoxybenzene". Synthesis of (E)-1-(1-heptenyl)-4-methoxybenzene via a one-pot hydroarylation of 1-heptyne. OrgSyn reproduced the reaction at 84% yield on 3.4 g scale (original: 84% at 173 mg scale) in THF. Yield matches the reported value exactly; scale-up proceeded without re-optimisation.

Platinum catalyzed hydrosilylation and palladium catalyzed cross-coupling: One-pot hydroarylation of 1-heptyne to (E)-1-(1-heptenyl)-4-methoxybenzene

Organic Syntheses · 2005

10.15227/orgsyn.081.0054