Department of Chemistry and Institute for Natural Sciences, Hanyang University, Seoul, 133-791, Korea.
Beilstein J Org Chem. 2013 Aug 22;9:1724-9. doi: 10.3762/bjoc.9.198. eCollection 2013.
Gold-catalyzed intermolecular couplings of sulfonylacetylenes with allyl ethers are reported. A cooperative polarization of alkynes both by a gold catalyst and a sulfonyl substituent resulted in an efficient intermolecular tandem carboalkoxylation. Reactions of linear allyl ethers are consistent with the [3,3]-sigmatropic rearrangement mechanism, while those of branched allyl ethers provided [3,3]- and [1,3]-rearrangement products through the formation of a tight ion-dipole pair.
本文报道了金催化的磺酰基乙炔与烯丙基醚的分子间偶联反应。炔烃通过金催化剂和磺酰基的协同极化作用，实现了高效的分子间串联碳烷氧基化反应。线性烯丙基醚的反应符合[3,3]-σ重排机理，而支链烯丙基醚则通过形成紧密的离子-偶极对，生成了[3,3]-和[1,3]-重排产物。
