%0 Journal Article
%A Larock, Richard C.
%A Tian, Qingping
%D 1998
%T Palladium-Catalyzed Annulation of Internal Alkynes by
Arene-Containing Vinylic Iodides and Triflates
%U https://acs.figshare.com/articles/journal_contribution/Palladium-Catalyzed_Annulation_of_Internal_Alkynes_by_Arene-Containing_Vinylic_Iodides_and_Triflates/3709131
%R 10.1021/jo972154b.s002
%2 https://ndownloader.figshare.com/files/5799684
%K Internal Alkynes
%K vinylic palladium
%K annulation process
%K vinylic substrate
%K acyclic vinylic iodides
%K intramolecular ring closure
%K triflate
%K alkyne
%K palladium catalyst
%K aryl group
%K oxidative addition
%K carbon moiety
%X In the presence of a palladium catalyst, internal alkynes undergo
carboannulation by cyclic and
acyclic vinylic iodides and triflates bearing a neighboring aromatic
ring to produce a variety of
carbocycles. For example, a number of
9,10-disubstituted-1,2,3,4-tetrahydrophenanthrenes have
been prepared in good yields through the palladium-catalyzed annulation
of internal alkynes by
2-phenyl-1-cyclohexenyl triflate (1) or
1-iodo-2-phenylcyclohexene (2). This annulation process
is
fairly general and highly regioselective. The process appears to
involve oxidative addition of the
vinylic substrate to Pd(0) to produce a vinylic palladium
intermediate, which adds the carbon moiety
to the less hindered end and the palladium to the more hindered end of
the alkyne, followed by
intramolecular ring closure onto the neighboring aryl group. The
scope and limitations of this
methodology are discussed.
%I ACS Publications