Ir‐Catalyzed Borylation of CH Bonds in N‐Containing Heterocycles: Regioselectivity in the Synthesis of Heteroaryl Boronate Esters | Zendy

Mkhalid Ibraheem A. I. | Zendy; Coventry David N. | Zendy; AlbesaJove David | Zendy; Batsanov Andrei S. | Zendy; Howard Judith A. K. | Zendy; Perutz Robin N. | Zendy; Marder Todd B. | Zendy

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Ir‐Catalyzed Borylation of CH 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).

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