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Ir‐Catalyzed Borylation of CH Bonds in N‐Containing Heterocycles: Regioselectivity in the Synthesis of Heteroaryl Boronate Esters
Author(s) -
Mkhalid Ibraheem A. I.,
Coventry David N.,
AlbesaJove David,
Batsanov Andrei S.,
Howard Judith A. K.,
Perutz Robin N.,
Marder Todd B.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200503047
Subject(s) - borylation , chemistry , regioselectivity , steric effects , catalysis , stereochemistry , substrate (aquarium) , combinatorial chemistry , medicinal chemistry , organic chemistry , aryl , alkyl , oceanography , geology
Blocking the way : Substitution at the 2‐position in pyridines and other N‐heterocycles blocks N‐coordination to an Ir center. This steric hindrance provides a substrate‐design criterion that allows the Ir‐catalyzed borylation of CH bonds, which can be followed by Suzuki–Miyaura cross‐coupling in a one‐pot reaction (see scheme; B 2 pin 2 =bis(pinacolato‐ O , O ′)diboron, dtbpy=4,4′‐ t Bu 2 ‐2,2′‐bipyridine).