Erratum: Application of the lithiation-borylation reaction to the preparation of enantioenriched allylic boron reagents and subsequent in situ conversion into 1,2,4-trisubstituted homoallylic alcohols with complete control over all elements of stereochemi

Full text of DOI:10.1021/ja102041s

Mechanism of C-F Reductive Elimination from
Palladium(IV) Fluorides [J. Am. Chem. Soc. 2010,
132, 3793–3807]. Takeru Furuya, Diego Benitez,
Therefore, as in the original paper, we characterize mechanism
4b as unlikely.
JA102348W
Ekaterina
Tkatchouk,
Alexandra
E.
Strom,
10.1021/ja102348w
Published on Web 04/05/2010
Pingping Tang, William A. Goddard III, and
Tobias Ritter*
Pages 3799-3800. The F values determined by Hammett
analysis in Figures 11-14 were calculated on the basis of the
natural logarithm (ln(kX/kH)). However, Hammett values are
calculated on the basis of the logarithm to the base 10 (log(kX/
kH)). The correct values are F1 ) -0.19 (originally reported as
-0.45, Figure 11), F2 ) -0.22 (originally reported as -0.52,
Figure 12), F3 ) +0.61 (originally reported as +1.41, Figure 13),
F ) +1.94 (originally reported as +4.47, Figure 14), and F )
-0.77 (originally reported as -1.78, Figure 14).
Application of the Lithiation-Borylation Reaction to
the Preparation of Enantioenriched Allylic Boron
Reagents and Subsequent in Situ Conversion into
1,2,4-Trisubstituted Homoallylic Alcohols with
Complete
Stereochemistry [J. Am. Chem. Soc. 2010, 132, 4025–
4028]. Martin Althaus, Adeem Mahmood,
Control
over
All
Elements
of
Jose´ Ramo´n Sua´rez, Stephen P. Thomas, and
Varinder K. Aggarwal*
The correction of the F values does not change the interpreta-
tion of the data or the conclusion of the paper because only the
numerical values but not the sign of the values change.
Structure 5 was incorrectly drawn as the wrong enantiomer.
The structure of compound 12 in Table 2 was the trimethyl tin
carbamate, not the tributyl tin carbamate as drawn. All
compounds described in Table 2 are now included in a revised
Supporting Information file (revised pp S39-S50).
Page 3804. In our third point in the Discussion subsection
“Mechanism of C-F Reductive Elimination from 1”, we
characterize mechanism 4b as unlikely based on Hammett
values. While the corrected Hammett value F2 ) -0.22 is
consistent with our conclusion, the following addition to that
paragraph bolsters our conclusion:
Supporting Information Available: Full experimental and
characterization data. This material is available free of charge
via the Internet at http://pubs.acs.org.
JA102041S
Computational analysis predicted a bond shortening of 0.01
Å of the Pd-N(pyridine/pyridinesulfonamide) bond in the
transition-state structure 1q, inconsistent with mechanism 4b.
10.1021/ja102041s
Published on Web 04/05/2010
9
5922 J. AM. CHEM. SOC. 2010, 132, 5922
10.1021/ja102348w  2010 American Chemical Society