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2005
C-C bond formation
O 0282
Ligand-Switchable Directing Effects of Tethered Alkenes in Nickel-Catalyzed
to Alkynes. — The reductive couplings of the alkynes (I) - bound via a
14- 057 Additions
methylene tether of variable length to a remote alkene functionality - to the aldehyde
(II) in the absence of an additive are shown to give only in the case of the tris-methylene
tethered alkyne (Ic) a high yield and regioselectivity in favor of the product (IIIc). In
the presence of a phosphine additive, the yields do not depend on the tether length, but
in this case only (Ic) reacts with complete preference to the other isomer (IVc). Highly
regioselective reductive couplings directed by a remote alkene are also observed for the
differently substituted alkynes (VIII). — (MILLER, K. M.; JAMISON*, T. F.; J. Am.
Chem. Soc. 126 (2004) 47, 15342-15343; Dep. Chem., MIT, Cambridge, MA 02139,
USA; Eng.) — Kieslich
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