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Synlett 2010(14): 2114-2118  
DOI: 10.1055/s-0030-1258521
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Ruthenium Carbene Mediated [2+2+2] Cyclotrimerizations

Álvaro Mallagaray, Sandra Medina, Gema Domínguez, Javier Pérez-Castells*
Facultad de Farmacia, Dpto. Química, Universidad San Pablo CEU, Urb. Montepríncipe, ctra. Boadilla km 5,300 Boadilla del Monte, 28668 Madrid, Spain
Fax: +34(91)3510496; e-Mail: jpercas@ceu.es;
Further Information

Publication History

Received 21 May 2010
Publication Date:
27 July 2010 (online)

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Abstract

Second-generation Grubbs’ catalyst and Hoveyda-Grubbs’ catalyst are able to catalyze both crossed [2+2+2] cyclotrimerization of diynes with alkynes and di- or trimerizations of diynes. Selection of the reaction conditions allows us to favor one particular process. The process is selective when applied to unsymmetric diynes.

Key words

cyclization - ruthenium - carbenes - alkynes - arenes

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    For details on the preparation of 1c and 1f, see Supporting Information.

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11

Ratio of isomers calculated by integration of well resolved signals in the ¹H NMR spectrum of the reaction crude

12

The work up of this reaction (entry 5, Table  [³] ) allowed the recovery of 50% of the catalyst used.