Prospect of Gold-Catalyzed Cyclization of Propargylureas on Solid Support

LA VENIA AGUSTINA; MEDRAN NOELIA S.; KRCHNAK VIKTOR; TESTERO SEBASTIÁN A.

Estambul

Congreso; EuCheMS Chemistry Congress; 2014

EuCheMS

Application of organometallic chemistry to solid-phase organic synthesis (SPOS) has increased substantially in the last decade.1 The advantages of SPOS are: easy purification by simple filtration, excessof reagents can be added to drive reactions to completion and amenability to automate among others.2 Hence, SPOS allows a rapid synthesis of a great number of compounds. On the other hand, in thelast years, research in homogeneous gold catalysis has reached a high level of development; however, the application of this metal to SPOS is very limited.3 Gold is a "soft" transition metal that isconsidered as one of the most powerful activators of a carbon-carbon triple bond due to the high binding energies of the alkyne-gold complexes.4 As a result, gold is strongly alkynophilic but it is not asoxophilic as most Lewis acids. This provides a remarkable advantage to the auric chemistry since oxygen, water, and alcohols are often well-tolerated5 making it easy to manipulate