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(Triphenyl phosphite)gold(I)-Catalyzed Intermolecular Hydroamination of Alkenes and 1,3-Dienes

Xavier Giner and Carmen Nájera*

*Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, Apartado 99, E-03080 Alicante, Spain, Email:

X. Giner, C. Nájera, Org. Lett., 2008, 10, 2919-2922.

DOI: 10.1021/ol801104w


Addition of sulfonamides to alkenes and conjugated dienes can be carried out using a low catalytic amount of (triphenyl phosphite)gold(I) chloride and silver triflate under thermal or microwave conditions and at r.t. in the case of dienes. Terminal alkenes undergo regioselective hydroamination at the internal carbon atom and dienes at the less substituted double bond.

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Concerning the conditions under MW (see Org. Lett.):
The pressure of 10 psi refers to the air used to refrigerate the vessel, and is not the pressure inside of the vial.

Concerning the acceleration under MW irradiation:
We have not optimised the reaction time under conventional heating, but have simply heated the reaction overnight. In some experiments we have used conventional heating for only 2 h and obtained similar results. So far, no MW effect can be deduced from these data.

Carmen Nájera, December 21, 2009

Key Words

amination, sulfonamides, microwave synthesis

ID: J54-Y2008-1980