Scope and limitations of the dual-gold-catalysed hydrophenoxylation of alkynes

• Adrián Gómez-Suárez,
• Yoshihiro Oonishi,
• Anthony R. Martin and
• Steven P. Nolan

Beilstein J. Org. Chem. 2016, 12, 172–178, doi:10.3762/bjoc.12.19

• /bjoc.12.19 Abstract Due to the synthetic advantages presented by the dual-gold-catalysed hydrophenoxylation of alkynes, a thorough study of this reaction was carried out in order to fully define the scope and limitations of the methodology. The protocol tolerates a wide range of functional groups, such

• in unsymmetrical alkynes can help to achieve high regioselectivity in the hydrophenoxylation. Keywords: cooperative catalysis; gold catalysis; hydrophenoxylation; N-heterocyclic carbene; vinyl ethers; Introduction During the last 30 years, N-heterocyclic carbenes (NHCs) have evolved from mere

• powerful catalysts for the construction of valuable organic molecules via the construction of C–C or C–O bonds [14][15][16][17][18][19][20][21][22][23]. In this regard, we have recently reported the use of [{Au(NHC)}2(µ-OH)][BF4] species as dual-activation catalysts for the hydrophenoxylation of alkynes

Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes

• Marcia E. Richard,
• Daniel V. Fraccica,
• Kevin J. Garcia,
• Erica J. Miller,
• Rosa M. Ciccarelli,
• Erin C. Holahan,
• Victoria L. Resh,
• Aakash Shah,
• Peter M. Findeis and
• Robert A. Stockland Jr.

Beilstein J. Org. Chem. 2013, 9, 2002–2008, doi:10.3762/bjoc.9.235

• compounds have been synthesized and investigated as single-component catalysts for the hydrophenoxylation of unactivated internal alkynes. Both carbene and phosphine-ligated compounds were screened as part of this work, and the most efficient catalysts contained either JohnPhos or IPr/SIPr. Phenols bearing

• ; gold; gold catalysis; hydrophenoxylation; silver-free; single component; solvent-free; Introduction The use of gold compounds to promote hydroelementation reactions has grown tremendously over the past few years [1][2][3][4][5]. Using this approach, a host of different organic substrates have been

• successfully functionalized. Despite the intense interest in this chemistry the addition of phenols to internal alkenes has rarely been investigated [1][5]. Recently, Sahoo reported the hydrophenoxylation of alkynes using a multicomponent catalyst comprised of AuCl3, JohnPhos as the supporting ligand, and