2014
DOI: 10.1246/cl.140888
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GaBr3-catalyzed Coupling between α-Iodo Esters with Alkynylstannanes under UV Irradiation

Abstract: A coupling between various alkynylstannanes with α-iodo esters was catalyzed by GaBr3 under UV irradiation conditions, for which a catalytic amount of GaBr3 was essential, and a radical coupling with the generated alkynylgallium species was involved. The desired α-alkynyl esters were selectively obtained even in the presence of an aryl–I bond, which is a reactive site in a conventional palladium-catalyzed system.

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Cited by 10 publications
(4 citation statements)
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“…In 2005, Oshima and coworkers discovered that alkynylindium reagents have similar reactivity than alkynylgallium reagents 29. Since Oshima's discovery, new applications of alkynylindium and alkynylgalliums have appeared 30…”
Section: Classical Methods For the Alkynylation Of Radicalsmentioning
confidence: 99%
“…In 2005, Oshima and coworkers discovered that alkynylindium reagents have similar reactivity than alkynylgallium reagents 29. Since Oshima's discovery, new applications of alkynylindium and alkynylgalliums have appeared 30…”
Section: Classical Methods For the Alkynylation Of Radicalsmentioning
confidence: 99%
“…However, the scope for alkynylation has been limited to α‐haloesters and amides to date. We found two reports, in which α‐alkynylation of a ketone is described, although there is only one reaction example in each report ,. One possible reason why a ketone has not been employed as a substrate would be decomposition or side‐reaction of the starting material and/or product caused by deprotonation of an acidic α‐proton under basic conditions applied in most cross‐coupling reactions.…”
Section: Figurementioning
confidence: 99%
“…1 Alkynylstannanes can be used as organometallic reagents to create diverse useful products through the modification of alkynyl or stannane groups. 2,3 Therefore, it is significant to develop efficient methods for the synthesis of alkynylstannanes. The most traditional method for the synthesis of alkynes is to deprotonate terminal alkynes with a strong base and then trap the resulting alkyne metals with an appropriate tin halide.…”
Section: Introductionmentioning
confidence: 99%