Organic Chemistry Seminar

Gold(I) complexes are the catalysts of choice for the cyclization of 1,n-enynes selective that proceed by selective activation of alkynes under mild conditions.1 We have applied gold(I) catalysis for total synthesis of the sesquiterpenes orientalol F and englerin A.2 Recently we have found that the intermolecular reaction of alkynes with alkenes catalyzed by gold(I) leads to cyclobutenes in the presence of cationic gold(I) catalysts bearing bulky phosphine ligands.3

Gold(I) complexes also promote the retrocyclopropanation of norcaradienes leading to gold(I) carbenes, which can be trapped with alkenes in new cyclopropanation reactions.4

New reactions of gold(I) carbenes generated under catalytic conditions from cycloheptatrienes and other intermolecular processes will be presented.

1. E. Jiménez-Núñez, A. M. Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350.

2. (a) E. Jiménez-Núñez, K. Molawi, A. M. Echavarren, Chem. Commun. 2009, 7327-7329. (b) K. Molawi, N. Delpont, A. M. Echavarren, Angew. Chem. Int. Ed. 2010, 49, 3517-3519.

3. V. López-Carrillo, A. M. Echavarren, J. Am. Chem. Soc. 2010, 132, 9292-9294.

4. (a) C. R. Solorio-Alvarado, A. M. Echavarren, J. Am. Chem. Soc. 2010, 132, 11881-11883. (b) Solorio-Alvarado, C. R.; Wang. Y.; Echavarren, A. M. J. Am. Chem. Soc. 2011, 133, 11952-11955.