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. 2015 Dec 21;54(52):15840-4.
doi: 10.1002/anie.201508912. Epub 2015 Nov 5.

Ligand-Enabled Catalytic C-H Arylation of Aliphatic Amines by a Four-Membered-Ring Cyclopalladation Pathway

Chuan He  1 , Matthew J Gaunt  2
Affiliations

Ligand-Enabled Catalytic C-H Arylation of Aliphatic Amines by a Four-Membered-Ring Cyclopalladation Pathway

Chuan He et al. Angew Chem Int Ed Engl. .

Abstract

A palladium-catalyzed CH arylation of aliphatic amines with arylboronic esters is described, proceeding through a four-membered-ring cyclopalladation pathway. Crucial to the successful outcome of this reaction is the action of an amino-acid-derived ligand. A range of hindered secondary amines and arylboronic esters are compatible with this process and the products of the arylation can be advanced to complex polycyclic molecules by sequential CH activation reactions.

Keywords: CH activation; amines; amino acids; homogeneous catalysis; palladium.

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