Advanced Organic Chemistry Practice Problems 2021 ((link)) -

Product: Cyclopentyl-4-trifluoromethylbenzene. Mechanism: Ni(0) oxidative addition into Ar–Br → transmetalation with alkyl-BF₃K (base-assisted) → Ir(III)* excited state reduces Ni(II) to Ni(0) via SET, closing cycle.

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Suddenly, the pathway cleared. The electrons flowed. The stereochemistry resolved itself. Product: Cyclopentyl-4-trifluoromethylbenzene

Draw the transition state for the thermal closure. Why is the disrotatory mode favored despite steric clash of methyl groups? Suddenly, the pathway cleared

Cyclopentadiene, Methyl vinyl ketone (MVK), Acetylene, and any monofunctional $\textC_1$ to $\textC_3$ reagents.

Cycle: Pd(II) ligation → C–H cleavage via concerted metalation-deprotonation (CMD) → oxidation with NFSI to Pd(IV) → reductive elimination to C–F bond. Ligand L1 creates a chiral pocket, blocking approach to less hindered C–Hs.

A linear enynone (R–C≡C–C(O)–CH=CH₂)