ORGANIC
LETTERS
2005
Vol. 7, No. 21
4553-4556
Intramolecular Additions of Alcohols
and Carboxylic Acids to Inert Olefins
Catalyzed by Silver(I) Triflate
Cai-Guang Yang, Nicholas W. Reich, Zhangjie Shi,† and Chuan He*
Department of Chemistry, The UniVersity of Chicago, 5735 South Ellis AVenue,
Chicago, Illinois 60637
Received May 9, 2005 (Revised Manuscript Received September 2, 2005)
ABSTRACT
Intramolecular additions of hydroxyl or carboxyl groups to inert olefins catalyzed by simple silver(I) triflate are described. Good to excellent
yields can be obtained for a range of substrates under relatively mild conditions. This reaction represents one of the simplest methods to
construct cyclic ethers or lactones.
Silver-catalyzed reactions have recently begun to emerge as
important methods for organic synthesis.1 Silver(I) salts have
been used as Lewis acids to catalyze a variety of transforma-
tions2-9 and also exhibit interesting activity in catalyzing
oxidation reactions.10 Silver(I) is known to interact with
unsaturated hydrocarbons,11 while the use of silver(I) salts
to activate such substrates has been primarily limited to
allenes12 and alkynes13 so far. We have discovered that
(7) For a selected example on silylene transfer reactions, see: Cirakovic,
J.; Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 9370-
9371.
† Current Address: Peking University, 202 Chengfu Road, Haidian
District, Beijing 100871, P. R. China.
(1) Yanagisawa, A. Lewis Acids in Organic Synthesis; Yamamoto, H.,
Ed.; Wiley-VCH: Weinheim, Germany, 2000; Vol. 2, Chapter 13.
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N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360-5361. (b) Hayashi,
T.; Uozumi, Y.; Yamazaki, A. Tetrahedron Lett. 1991, 32, 2799-2802.
(3) For selected examples on aldehyde allylation, see: (a) Yanagisawa,
A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996,
118, 4723-4724. (b) Itami, K.; Kamei, T.; Mineno, M.; Yoshida, J. Chem.
Lett. 2002, 1084-1085.
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N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018-
4019. (b) Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost,
C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088-2098. (c) Loncaric, C.;
Manabe, K.; Kobayashi, S. AdV. Synth. Catal. 2003, 345, 475-477.
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C.-J. Synlett. 2004, 1472-1483.
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(11) For reviews encompassing Ag(I)-alkene complexes, see: (a)
Bennett, M. A. Chem. ReV. 1962, 62, 611-652. (b) Quinn, H. W.; Tsai, J.
H. AdV. Inorg. Radiochem. 1969, 12, 217-373. (c) Beverwijk, C. D. M.;
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A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966-5968. (c) Huang, Q.;
Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437-3444. (d)
Harrison, T. J.; Dake, G. R. Org. Lett. 2004, 6, 5023-5026.
(6) For selected examples on [3 + 2] cycloaddition of azomethine ylides,
see: (a) Longmire, J. M.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2002,
124, 13400-13401. (b) Kno¨pfel, T. F.; Aschwanden, P.; Ichikawa, T.;
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10.1021/ol051065f CCC: $30.25
© 2005 American Chemical Society
Published on Web 09/21/2005