Page 10 - Organogold Reactivity with Palladium, Nickel, and Rhodium: Transmetalation, Cross-Coupling, and Dual Catalysis

Organogold Dual Metal Catalysis Hirner et al.

fundamental knowledge about the stability and reactivity of 4 Sammis, G. M.; Danjo, H.; Jacobsen, E. N. Cooperative Dual Catalysis: Application to the
Highly Enantioselective Conjugate Cyanation of Unsaturated Imides. J. Am. Chem. Soc.
organogold compounds in the presence of other transition 2004, 126, 9928–9929.
þ
metals and potentially competing Brønsted acids. Pioneer- 5 Ma, S.; Shi, Z. Pd(0)/Ag -Cocatalyzed Cyclization Reaction of 1,2-Allenic Carboxylic Acids
with Aryl/Alkenyl Halides. An Efficient Synthesis of Butenolides. J. Org. Chem. 1998, 63,
ing studies in gold catalysis have given the synthetic com- 6387–6389.
munity a variety of methods to form carbongold bonds; 6 For contextual examples of dual catalysis not involving gold, see: (a) Jacobsen, E. N.
Asymmetric Catalysis of Epoxide Ring-Opening Reactions. Acc. Chem. Res. 2000, 33,
in light of ongoing work with dual-metal gold reactivity in 421–431. (b) Liu, Z.; Henderson, J. A.; Sasaki, T.; Kishi, Y. Dramatic Improvement in
Catalyst Loadings and Molar Ratios of Coupling Partners for Ni/Cr-Mediated Coupling
our group and others, we are beginning to access a corre-
Reactions: Heterobimetallic Catalysts. J. Am. Chem. Soc. 2009, 131, 16678–16680.
spondingly diverse set of tools with which to functionalize (c) Shibasaki, M.; Yamamoto, Y. Multimetallic Catalysts in Organic Synthesis; Wiley-VCH:
Germany, 2004. (d) Zanardi, A.; Mata, J. A.; Peris, E. Well-Defined Ir/Pd Complexes with a
them. Triazolyl-diylidene Bridge as Catalysts for Multiple Tandem Reactions. J. Am. Chem. Soc.
2009, 131, 14531–14537.
7 Hashmi, A. S. K. Gold-Catalyzed Organic Reactions. Chem. Rev. 2007, 107, 3180–3211.
BIOGRAPHICAL INFORMATION 8 Li, Z.; Brouwer, C.; He, C. Gold-Catalyzed Organic Transformations. Chem. Rev. 2008,
108,3239–3265.
Joshua J. Hirner was born in 1986 in Hannibal, Missouri. 9 Gorin, D. J.; Sherry, B. D.; Toste, F. D. Ligand Effects in Homogeneous Au Catalysis. Chem.
He received his B.S. in Chemistry (2009) from Truman State Rev. 2008, 108, 3351–3378.
University under the guidance of Professors Anne E. Moody and 10 For an early example, see: (a) Díaz-Requejo, M. M.; P erez, P. J. Copper, Silver, and Gold-
Based Catalysts for Carbene Addition or Insertion Reactions. J. Organomet. Chem. 2005,
Barbara K. Kramer. He is currently a graduate student working with 690,5441–5460.
Professor Suzanne A. Blum to investigate the combined reactivity 11 For two early examples of Au(I)/Au(III) cross-coupling using Selectfluor as an oxidant, see:
of gold and nickel. (a) Zhang, G.; Peng, Y.; Cui, L.; Zhang, L. Gold-Catalyzed Homogeneous Oxidative Cross-
Coupling Reactions. Angew. Chem., Int. Ed. 2009, 48, 3112–3115. (b) Zhang, G.; Cui, L.;
Yili Shi was born in Jilin, China in 1984. He received his B.S. in Wang, Y.; Zhang, L. Homogeneous Gold-Catalyzed Oxidative Carboheterofunctionalization
Chemistry (2005) from the University of California, Berkeley, working of Alkenes. J. Am. Chem. Soc. 2010, 132, 1474–1475.
in the lab of Professor Jonathan A. Ellman. He is currently a Ph.D. 12 Akiyama, K.; Catellani, M.; Fu, G. C.; Guit an, E.; Hatano, M.; Larock, R. C.; Ma, S.; Mikami,
M.; Miura,M.; Nakamura,I.; Netherton, M. R.;Nolan,S.P.; Pe~ na, D.; P erez, D.; Satoh, T.;
student with Professor Suzanne A. Blum where he develops dual- Viciu, M. S.; Yamamoto, Y. Topics in Organic Synthesis: Palladium in Organic Synthesis;
catalytic reactions with design motivated by mechanistic insight. Tsuji, J., Ed.; Springer Verlag: Berlin.
13 Shi, Y.;Peterson, S. M.;Haberaecker,W.W.; Blum,S.A.Alkynes as Stille Reaction
Suzanne A. Blum received a B.S. in Chemistry at the University Pseudohalides: Gold- and Palladium-Cocatalyzed Synthesis of Tri- and Tetra-Substituted
of Michigan and a Ph.D. from the University of California, Berkeley, Olefins. J. Am. Chem. Soc. 2008, 130, 2168–2169.
under the supervision of Professors Robert G. Bergman and 14 Shirakawa, E.; Yoshida, H.; Nakao, Y.; Hiyama, T. Palladium-Catalyzed Dimerization-
Carbostannylation of Alkynes: Synthesis of Highly Conjugated Alkenylstannanes. J. Am.
Jonathan A. Ellman. After an NIH postdoctoral fellowship with Chem. Soc. 1999, 121, 4290–4291.
Professor Christopher T. Walsh at the Harvard Medical School, 15 Yoshida, H.; Shirakawa, E.; Nakao, Y.; Honda, Y.; Hiyama, T. Dimerization-Carbostanny-
she joined the Chemistry Department of the University of lation of Alkynes Catalyzed by a Palladium-Diimine Complex: Regioselectivity, Stereo-
selectivity and Mechanism. Bull. Chem. Soc. Jpn. 2001, 74,637–647.
California, Irvine in 2006. Her research interests include organo-
16 Porcel, S.; Echavarren, A. M. Intramolecular Carbostannylation of Alkynes Catalyzed by
metallic catalysis and single-molecule fluorescence microscopy. Silver(I) Species. Angew. Chem., Int. Ed. 2007, 46, 2672–2676.
17 Shi, Y.; Ramgren, S. D.; Blum, S. A. Palladium-Catalyzed Carboauration of Alkynes and
Palladium/Gold Cross-Coupling. Organometallics 2009, 28, 1275–77.
We thank our colleagues at the University of California, Irvine for
18 For examples of directed transmetalations from Au, see: Contel, M.; Stol, M.; Casado,
helpful conversations regarding the investigations described in this M. A.; van Klink, G. P. M.; Ellis, D. D.; Spek, A. L.; van Koten, G. A Bis(ortho-
amine)arylGold(I) Compound as an Efficient, Nontoxic, Arylating Reagent. Organome-
Account. Funding for our research program has been generously
tallics 2002, 21, 4556–4559.
providedbythe NationalScienceFoundationviaaCAREERawardfor 19 Casado, A. L.; Espinet, P. A Novel Reversible Aryl Exchange Involving Two Organometallics:
Mechanism of the Gold(I)-Catalyzed Isomerization of trans-[PdR 2 L 2 ]Complexes (R = Aryl,
S.A.B. (CHE-0748312) and a Graduate Research Fellowship for J.J.H. L=SC 4 H 8 ). Organometallics 1998, 17, 3677.
(NSF-2010105893), by the Allergan Foundation and University of 20 For an early example of dual Au/Pd dual reactivity that may have involved an organogold
intermediate, see: Jones, L. A.; Sans, S.; Laguna, M. Gold Compounds as Efficient Co-
California Regents through fellowships for Y.S., by the donors of the Catalysts in Paladium-Catalysed Alkynylation. Catal. Today 2007, 122, 403–406.
Petroleum Research Fund (administered by the American Chemical 21 Hashmi, A.S.K.; Lothsch€ utz, C.; D€ opp, R.; Rudolph, M.; Ramamurthi, T. D.; Rominger, F.
Gold and Palladium Combined for Cross-Coupling. Angew. Chem., Int. Ed. 2009, 48,
Society, 46285-G1), and by the University of California, Irvine. 8243–8243.
22 Podder, S.;Choudhury, J.; Roy, U. K.;Roy, S.Dual-Reagent Catalysiswithin IrSn Domain:
Highly Selective Alkylation of Arenes and Heteroarenes with Aromatic Aldehydes. J. Org.
FOOTNOTES
Chem. 2007, 72, 3100–3103.
*To whom correspondence should be addressed. E-mail: blums@uci.edu. 23 Trost, B. M.; Luan, X. Contemporaneous Dual Catalysis by Coupling Highly Transient
Nucleoplilic and Electrophilic Intermediates Generated in Situ. J. Am. Chem. Soc. 2011,
133,1706–1709.
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