Anionic and zwitterionic copper(i) complexes incorporating an anionic N-heterocyclic carbene decorated with a malonate backbone: Synthesis, structure and catalytic applications

Article abstract of DOI:10.1039/c3dt32919d

The anionic malonate-derived N-heterocyclic carbenes (maloNHCs) react cleanly and rapidly with copper chloride to generate the anionic complexes of type [(maloNHC)CuCl]·Li, which crystallize in the solid state either in an oligomeric trimer arrangement or

Full text of DOI:10.1039/c3dt32919d

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
Anionic and zwitterionic copper(I) complexes incorporating an anionic N-
Heterocyclic Carbene decorated with a malonate backbone: synthesis,
structure and catalytic applications
Vincent César,*a,b Cécile Barthes,a,b Yoann C. Farre,c Stéphane V. Cuisiat,c Bernard Y.
Vacher,c Rémy Brousses,a,b Noël Lugan*a,b and Guy Lavigne*a,b
a CNRS, LCC (laboratoire de Chimie de Coordination), 205 route de Narbonne, F-31077 Toulouse Cedex 4,
France
b Université de Toulouse, UPS, INPT, 31077 Toulouse, France
c Pierre Fabre Research Center, 17 avenue Jean Moulin, 81106 Castres Cedex, France
Supporting Information
Contents
1H and 13C{1H} NMR spectra of (1b)·H
1H and 13C{1H} NMR spectra of (1b)·Li
1H and 13C{1H} NMR spectra of (2a)·Li in THF-d8
1H and 13C{1H} NMR spectra of (2a)·Li in acetone-d6
1H and 13C{1H} NMR spectra of (2b)·Li
1H and 13C{1H} NMR spectra of 3aa
2
3
4
5
6
7
1H and 13C{1H} NMR spectra of 3ab
8
1H and 13C{1H} NMR spectra of 3ac
9
1H and 13C{1H} NMR spectra of 3ad
1H and 13C{1H} NMR spectra of 3ae
1H and 13C{1H} NMR spectra of 3af
1H and 13C{1H} NMR spectra of 3ba
1H and 13C{1H} NMR spectra of 3bb
1H and 13C{1H} NMR spectra of 3bd
1H and 13C{1H} NMR spectra of 3be
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11
12
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15
16
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A perpective view of the cell packing along the a axis for complex
[2b].Li(thf)3 showing the occurrence of channels (red circles) along that
direction
1

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1H NMR spectrum of (1b)·H (300 MHz, CDCl3)
13C {1H} NMR spectrum of (1b)·H (75.5 MHz, CDCl3)
2

Electronic Supplementary Material (ESI) for Dalton Transactions
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1H NMR spectrum of (1b)·Li (400 MHz, THF-d8)
13C {1H} NMR spectrum of (1b)·Li (100.5 MHz, THF-d8)
3

Electronic Supplementary Material (ESI) for Dalton Transactions
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1H NMR spectrum of [2a]·Li (400 MHz, THF-d8)
Et2O
Et2O
13C {1H} NMR spectrum of [2a]·Li (100.5 MHz, THF-d8)
4

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of [2a]·Li (400 MHz, acetone-d6)
13C {1H} NMR spectrum of [2a]·Li (100.5 MHz, acetone-d6)
5

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of [2b]·Li (400 MHz, THF-d8)
Et2O
Et2O
13C {1H} NMR spectrum of [2b]·Li (100.5 MHz, THF-d8)
6

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3aa (400 MHz, CDCl3)
13C {1H} NMR spectrum of 3aa (100.5 MHz, CDCl3)
7

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3ab (300 MHz, CDCl3)
13C {1H} NMR spectrum of 3ab (75.5 MHz, CDCl3)
8

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3ac (300 MHz, CDCl3)
13C {1H} NMR spectrum of 3ac (75.5 MHz, CDCl3)
9

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3ad (300 MHz, CDCl3)
13C {1H} NMR spectrum of 3ad (75.5 MHz, CDCl3)
10

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3ae (400 MHz, CDCl3)
13C {1H} NMR spectrum of 3ae (100.5 MHz, CDCl3)
11

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3af (400 MHz, CDCl3)
13C {1H} NMR spectrum of 3af (100.5 MHz, CDCl3)
12

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3ba (400 MHz, CDCl3)
13C {1H} NMR spectrum of 3ba (100.5 MHz, CDCl3)
13

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3bb (400 MHz, CDCl3)
13C {1H} NMR spectrum of 3bb (100.5 MHz, CDCl3)
14

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3bd (400 MHz, CDCl3)
13C {1H} NMR spectrum of 3bd (100.5 MHz, CDCl3)
15

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
1H NMR spectrum of 3be (400 MHz, CDCl3)
13C {1H} NMR spectrum of 3be (100.5 MHz, CDCl3)
16

Electronic Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2013
A perpective view of the cell packing along the a axis for complex [2b].Li(thf)3 showing the
occurrence of channels (red circles) along that direction
17