A novel macrocyclization procedure is developed on the basis of a domino process. Thus, treatment of linear diiodide I under defined conditions gave a 15-membered m,m-cyclophane via aryl-aryl bond formation. Two distinct cross-coupling manifolds, Miyaura's arylboronic ester synthesis and intramol. Suzuki reaction, proceed in an ordered fashion. Concn. is an important factor for the success of this process. [on SciFinder (R)]
Title
A Novel Synthesis of Biaryl-Containing Macrocycles by a Domino Miyaura Arylboronate Formation: Intramolecular Suzuki Reaction
Published in
Organic Letters
Volume
2
Issue
22
Pages
3477-3480
Date
2000
ISSN
1523-7060
Note
CAN 134:29690
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
13139-15-6; 113850-71-8; 312493-94-0; 312493-98-4 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of biaryl-contg. macrocycles by a domino Miyaura arylboronate formation:intramol. Suzuki reaction); 312493-95-1P; 312493-96-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of biaryl-contg. macrocycles by a domino Miyaura arylboronate formation:intramol. Suzuki reaction); 312493-97-3P; 312493-99-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of biaryl-contg. macrocycles by a domino Miyaura arylboronate formation:intramol. Suzuki reaction)
