ol5b02482_si_001.pdf (5.8 MB)
Synthesis of E‑Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B‑Alkenyl-9-borabicyclo[3.3.1]nonanes
journal contribution
posted on 2015-10-02, 00:00 authored by Thomas Di Franco, Alexandre Epenoy, Xile HuThe
first Ni-catalyzed Suzuki–Miyaura coupling of alkyl
halides with alkenyl-(9-BBN) reagents is reported. Both primary and
secondary alkyl halides including alkyl chlorides can be coupled.
The coupling method can be combined with hydroboration of terminal
alkynes, allowing the expedited synthesis of functionalized alkyl
alkenes from readily available alkynes with complete (E)-selectivity in one pot. The method was applied to the total synthesis
of (±)-Recifeiolide, a natural macrolide.