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Regioselective ortho ‐Palladation of [2.2]Paracyclophane Scaffolds: Accessing Planar and Central Chiral N,C‐Palladacycles
Author(s) -
Zippel Christoph,
Bartholomeyzik Teresa,
Friedmann Christian,
Nieger Martin,
Hassan Zahid,
Bräse Stefan
Publication year - 2021
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.202101066
Subject(s) - regioselectivity , chemistry , bimetallic strip , amine gas treating , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
In this report, we describe a series of cyclophanyl‐derived mono‐ and binuclear N,C‐palladacycles by regioselective ortho ‐palladation of amine‐functionalized [2.2]paracyclophanes. Employing Pd(OAc) 2 followed by LiCl and with the subsequent modular treatment of Ph 3 P, Cy 3 P, and (Ph 2 PCH 2 ) 2 , this strategy allows to prepare stable cyclophanyl‐derived planar and central chiral N,C‐palladacycles in a highly selective manner. The regioselective ortho ‐palladation mono‐ and bimetallic product formation was analyzed by detailed spectroscopic techniques, mass spectrometry and unambiguously confirmed by single‐crystal X‐ray analysis.