Synthesis of <i>E</i>‑Alkyl Alkenes
from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides
with B‑Alkenyl-9-borabicyclo[3.3.1]nonanes
Thomas Di Franco
Alexandre Epenoy
Xile Hu
10.1021/acs.orglett.5b02482.s001
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_i_E_i_Alkyl_Alkenes_from_Terminal_Alkynes_via_Ni_Catalyzed_Cross_Coupling_of_Alkyl_Halides_with_B_Alkenyl_9_bora_bicyclo_3_3_1_nonanes/2126560
The
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 (<i>E</i>)-selectivity in one pot. The method was applied to the total synthesis
of (±)-Recifeiolide, a natural macrolide.
2015-10-02 00:00:00
alkyl halides
functionalized alkyl alkenes
method
alkyne
synthesis