Direct Access to 4,5 ‐ Disubstituted [2.2]Paracyclophanes by Selective  ortho ‐Halogenation with Pd‐Catalyzed C–H Activation | Zendy

Kramer Joshua J. P. | Zendy; Yildiz Ceylan | Zendy; Nieger Martin | Zendy; Bräse Stefan | Zendy

Premium

Direct Access to 4,5 ‐ Disubstituted [2.2]Paracyclophanes by Selective ortho ‐Halogenation with Pd‐Catalyzed C–H Activation

Author(s) -

Kramer Joshua J. P.,

Yildiz Ceylan,

Nieger Martin,

Bräse Stefan

Publication year - 2014

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201301723

Subject(s) - halogenation , chemistry , enantiopure drug , catalysis , selectivity , steric effects , palladium , aldehyde , chemoselectivity , combinatorial chemistry , medicinal chemistry , organic chemistry , enantioselective synthesis

A palladium‐catalyzed protocol for the halogenation of [2.2]paracyclophanes by C–H activation is described, and ortho selectivity is achieved with an O ‐methyloxime directing group. Bromination and iodination of the sterically demanding [2.2]paracyclophane proceed in good yields with inexpensive and readily available N ‐halosuccinimides. Deprotection of the O ‐methyloximes yields ortho ‐halogenated aldehydes as attractive intermediates for the modular synthesis of 4,5‐disubstituted [2.2]paracyclophanes. The synthetic value of this protocol was demonstrated by exemplary conversions of the carbaldehyde and halogen site. Additionally, early stage resolution and subsequent bromination/deprotection provides the brominated aldehyde in enantiopure form.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research