ACS Catalysis
Research Article
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(
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(19) For relevant examples of catalytic alkyne hydrations involving
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(20) Although compound 1c has been previously described in the
literature, it was not fully characterized: Profft, E.; Georgi, W. Justus
Liebigs Ann. Chem. 1961, 643, 136−144 . Complete details of its
synthesis and full characterization data are now included in the
Experimental Section of this article..
(21) Related zwitterionic imidazolium salts have been previously
synthesized following this route. See, for example: Moore, L. R.;
Cooks, S. M.; Anderson, M. S.; Schanz, H.-J.; Griffin, S. T.; Rogers, R.
D.; Kirk, M. C.; Shaughnessy, K. H. Organometallics 2006, 25, 5151−
5158.
(
9
́
́
́
́
́
́
́ ́
Katho, A.; Joo,
2
9
3
(
873−9882. (f) Kumar, P.; Cisarova, I. J. Organomet. Chem. 2013, 735,
2−37.
10) The synthesis and structural characterization of the highly
water-soluble bis protic gold(I)-NHC complex [Au(C H N ) ]Cl
C H N = imidazol-2-ylidene) has also been described: Kunz, P. C.;
3
4
2 2
(
3 4 2
Wetzel, C.; Ko
0, 35−37.
11) Gold complexes containing hydrophobic NHC ligands have also
̈
gel, S.; Kassack, M. U.; Spingler, B. Dalton Trans. 2011,
4
(
been applied in the catalytic hydration of alkynes and nitriles, as well as
the Meyer−Schuster rearrangement of propargylic alcohols, in
aqueous environments: (a) Schneider, S. K.; Herrmann, W. A.;
Herdtweck, E. Z. Anorg. Allg. Chem. 2003, 629, 2363−2370. (b) de
Frem
Organometallics 2007, 26, 1376−1385. (c) Marion, N.; Ramon
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́
Marion, N.; Nolan, S. P. Tetrahedron 2009, 65, 1767−1773.
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A.; Zanoni, G.; Nolan, S. P. Organometallics 2010, 29, 3665−3668.
h) Ramon, R. S.; Gaillard, S.; Poater, A.; Cavallo, L.; Slawin, A. M. Z.;
(
́
8
́
(
́
(
́
(22) The intermediate silver(I) complex I could be isolated in 90%
Nolan, S. P. Chem.Eur. J. 2011, 17, 1238−1246. (i) Merlini, V.;
yield from the reaction of 2b with Ag O and TBACl in refluxing
2
Gaillard, S.; Porta, A.; Zanoni, G.; Vidari, G.; Nolan, S. P. Tetrahedron
dichloromethane. However, this compound was obtained with a
relatively low purity because of the presence of minor amounts of the
́ ́
Lett. 2011, 52, 1124−1127. (j) Gomez-Suarez, A.; Oonishi, Y.; Meiries,
3
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dx.doi.org/10.1021/cs4009144 | ACS Catal. 2013, 3, 3086−3098