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. 2017 Feb 16;53(15):2315-2318.
doi: 10.1039/c6cc09794d.

Accessing alternative reaction pathways of the intermolecular condensation between homo-propargyl alcohols and terminal alkynes through divergent gold catalysis

Courtney A Smith  1 , Stephen E Motika  1 , Lukasz Wojtas  1 , Xiaodong Shi  1
Affiliations

Accessing alternative reaction pathways of the intermolecular condensation between homo-propargyl alcohols and terminal alkynes through divergent gold catalysis

Courtney A Smith et al. Chem Commun (Camb). .

Abstract

An intermolecular condensation of alkynols and terminal alkynes is reported. Using IPrAuNTf2, an efficient Au-catalyzed cyclization-alkynylation strategy furnishes (2-arylalkynyl) cyclic ethers in moderate to excellent yields (up to 94%). This strategy is extended to the synthesis of functionalized 2,3-dihydrooxepines via the sequential Au-catalyzed ring expansion of the cyclic ether substrates.

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Figures

Figure 1
Figure 1
Reaction kinetic profile
Figure 2
Figure 2
Exploration of reaction mechanism
Scheme 1
Scheme 1
Gold-catalyzed C-C multiple bond activation
Scheme 2
Scheme 2
Proposed reaction pathways
See this image and copyright information in PMC

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