Erratum: Carbon-heteroatom coupling using Pd-PEPPSI complexes (Organic Process Research and Development (2014) 18 (180-190) DOI: 10.1021/op400278d)

Full text of DOI:10.1021/op500093w

Addition/Correction
pubs.acs.org/OPRD
Correction to Carbon−Heteroatom Coupling Using Pd-PEPPSI
Complexes
Cory Valente, Matthew Pompeo, Mahmoud Sayah, and Michael G. Organ*
Org. Process Res. Dev. 2014, 18, 180−190. DOI: 10.1021/op400278d
1
. On page 188, in the paragraph starting in the first column at
OMe
the bottom of page 188, the catalyst name “Pd-PEPPSI-IPr*
OMe
(
101)” should be replaced by [Pd(IPr* )(acac)Cl] (101) so
that it reads as follows:
In a related study, the same group reported the couplings of
chloroanisole to a selection of aniline derivatives (leading to 58,
6
0 and 103) using modified IPr ligands, and comparisons were
made to the performance of Pd-PEPPSI-IPent (1) in the same
couplings but using different reaction conditions (Table 12).40
Figure 3. Pd−NHC precatalysts reported by Nolan and co-workers.
Table 12. Published comparison of Pd-PEPPSI-IPent (1)
with [Pd(IPr* )(acac)Cl] (101) under different reaction
conditions
OMe
3. Also related to this, Table 12 on page 188 in the
manuscript should be replaced by the corrected table and the
table title above.
a
When the same reaction was conducted in DME at 80 °C, 62% yield
b
was obtained. When the same reaction was conducted in DME at 80
°C using 85, 62% yield was obtained.
The reactivity of [Pd(IPr*OMe)(acac)Cl] (101) was reported by
the authors as high and on par with that of Pd-PEPPSI-IPent (1)
using the comparatively low catalyst loading as their
justification. Given that different reaction conditions were
used, comparisons in reactivity cannot be based on TON. Aryl
amination reaction conditions employing soluble, highly
aggressive tert-butoxide and its derivatives cannot be drawn
into comparisons with reactions performed using mild,
insoluble carbonate base. For example, the reaction in Scheme
4
requires approximately 24 h using Pd-PEPPSI-IPr (2) to
complete using carbonate base at 80 °C; the same reaction
t
21
using KO Bu completes in just 15 s at RT! If the same catalyst
performs vastly different under different reaction conditions,
any attempted comparison between catalysts under different
reactions conditions holds little value.
2. Related to this, Figure 3 on page 188 in the manuscript
should be replaced by the corrected Figure below:
Published: March 24, 2014
©
2014 American Chemical Society
559
dx.doi.org/10.1021/op500093w | Org. Process Res. Dev. 2014, 18, 559−559