Highly regiocontrolled Pd-catalyzed cross-coupling reaction of terminal alkynes and allenylphosphine oxides.
J Org Chem
; 68(16): 6251-6, 2003 Aug 08.
Article
em En
| MEDLINE
| ID: mdl-12895057
ABSTRACT
The cross-coupling of a variety of terminal alkynes 1 with allenylphosphine oxides 2 catalyzed by a Pd(OAc)(2)-TDMPP system provided conjugated endo-enynes 3 solely, while the TCPC-catalyzed reaction of the same regents led to the exclusive formation of exo-isomers 4. The mechanistic rationale for these selective transformations was proposed. Synthetic usefulness of the prepared exo-enyne 4 was demonstrated in the synthesis of multisubstituted diarylbenzylphosphine oxides 5 via the Pd-catalyzed [4+2]-benzannulation reaction.
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2003
Tipo de documento:
Article