Issue 10, 2015

2,2′-Bipyridyl formation from 2-arylpyridines through bimetallic diyttrium intermediate

Abstract

An alkylyttrium complex supported by an N,N′-bis(2,6-diisopropylphenyl)ethylenediamido ligand, (ArNCH2CH2NAr)Y(CH2SiMe3)(THF)2 (1, Ar = 2,6-iPr2C6H3), activated an ortho-phenyl C–H bond of 2-phenylpyridine (2a) to form a (2-pyridylphenyl)yttrium complex (3a) containing a five-membered metallacycle. Subsequently, a unique C(sp2)–C(sp2) coupling of 2-phenylpyridine proceeded through a bimetallic yttrium intermediate, derived from an intramolecular shift of the yttrium center to an ortho-position of the pyridine ring in 3a, to yield a bimetallic yttrium complex (4a) bridged by two-electron reduced 6,6′-diphenyl-2,2′-bipyridyl. Aryl substituents at the ortho-position of the pyridine ring were key in order to destabilize the μ,κ2-(C,N)-pyridyldiyttrium intermediate prior to the C(sp2)–C(sp2) bond formation.

Graphical abstract: 2,2′-Bipyridyl formation from 2-arylpyridines through bimetallic diyttrium intermediate

Supplementary files

Article information

Article type
Edge Article
Submitted
02 May 2015
Accepted
17 Jul 2015
First published
17 Jul 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 5394-5399

2,2′-Bipyridyl formation from 2-arylpyridines through bimetallic diyttrium intermediate

Y. Shibata, H. Nagae, S. Sumiya, R. Rochat, H. Tsurugi and K. Mashima, Chem. Sci., 2015, 6, 5394 DOI: 10.1039/C5SC01599E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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