In:
Angewandte Chemie International Edition, Wiley, Vol. 61, No. 47 ( 2022-11-21)
Abstract:
Controlling regioselectivity in C−H functionalizations is a key challenge in chemical method development. In arenes, functionalizations are most difficult to direct towards the C−H group furthest away from a substituent, in its para position. We herein demonstrate how the para ‐C−H arylation of anilines with non‐activated aryl halides, elusive to date, is achieved by a base‐assisted “metalla‐tautomerism” approach. A proton is abstracted from the aniline substrate and replaced by an arylpalladium species, generated from the aryl halide coupling partner. In this step, the palladium is directed away from the N ‐ to the tautomeric para ‐C−H position by a large phosphine ligand combined with a triphenylmethyl shielding group. The triphenylmethyl group is easily installed and removed, and can be recycled.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.202210009
Language:
English
Publisher:
Wiley
Publication Date:
2022
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7