Subscribe to RSS
DOI: 10.1055/s-0033-1341176
Rhodium-Catalyzed Addition of Arylboronic Acids to Alkenylazaarenes
A Second-Generation Ligand for the Enantioselective Rhodium-Catalyzed Addition of Arylboronic Acids to Alkenylazaarenes.
Chem. Commun. 2014;
50: 2865-2868
Publication History
Publication Date:
17 April 2014 (online)
Key words
asymmetric 1,4-arylation - boronic acids - alkenylazaarenes - chiral diene ligands - rhodium
Significance
In recent years, alkenylazaarenes have been identified as promising substrates in transition-metal-catalyzed 1,4-additions with the ability to mimic reaction profiles of α,β-unsaturated carbonyls. Therein, the authors exploit a broad variety of β-substituted alkenylazaarenes for a rhodium-catalyzed 1,4-arylation, where a refined 2,4,6-trialkylanilide containing a chiral diene ligand is responsible for efficient transfer of chirality.
#
Comment
In general, high to almost perfect enantioselectivities were observed for the 1,4-arylation of β-alkenylazaarenes. Furthermore, the high value of the transformation is demonstrated by a remarkable functional group tolerance on each position. In particular, the efficiency of both electron-rich and -poor heterocycles allows rapid access to a broad variety of high-value enantioenriched chiral azaarene products.
#
#