Erratum: Markovnikov-selective hydroboration of olefins catalyzed by a copper N-heterocyclic carbene complex (Organometallics (2019) 38:17 (3322-3326) DOI: 10.1021/acs.organomet.9b00394)

Article abstract of DOI:10.1021/acs.organomet.0c00629

It has come to our attention that some of the products listed in Table 2 of the article and in eq 1 have the incorrect stereochemistry. The reactions of alkynes with HBpin give the linear E-olefin products, not the branched products as were shown. 1H NMR spectra clearly show two doublets with a large J (18 Hz) for the trans-hydrogens of the alkene product. A DEPT-135 spectrum also confirms that CH and not CH₂ is present. Corrected eq 1, Table 2, TOC graphic are shown. Note that the alkene addition products are correctly assigned as branched, displaying a doublet and a quartet for the methyl and methane groups, respectively. NMR spectra for all products are included in the revised Supporting Information. We thank Prof. Jaesook Yun for pointing out this error, as her group has worked on related copper borylations for many years.

Full text of DOI:10.1021/acs.organomet.0c00629

pubs.acs.org/Organometallics
Addition/Correction
Correction to Markovnikov-Selective Hydroboration of Olefins
Catalyzed by a Copper N‑Heterocyclic Carbene Complex
Tarah A. DiBenedetto, Astrid M. Parsons, and William D. Jones*
Organometallics 2019, 38 (17), 3322−3326. DOI: 10.1021/acs.organomet.9b00394
Cite This: https://dx.doi.org/10.1021/acs.organomet.0c00629
Read Online
sı
*
Metrics & More
Article Recommendations
Supporting Information
ACCESS
t has come to our attention that some of the products listed in
Table 2 of the article and in eq 1 have the incorrect
I
stereochemistry. The reactions of alkynes with HBpin give the
linear E-olefin products, not the branched products as were
shown. 1H NMR spectra clearly show two doublets with a large J
(18 Hz) for the trans-hydrogens of the alkene product. A DEPT-
135 spectrum also confirms that CH and not CH2 is present.
Corrected eq 1, Table 2, TOC graphic are shown. Note that the
alkene addition products are correctly assigned as branched,
displaying a doublet and a quartet for the methyl and methane
groups, respectively. NMR spectra for all products are included
in the revised Supporting Information. We thank Prof. Jaesook
Yun for pointing out this error, as her group has worked on
related copper borylations for many years.1
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge at
https://pubs.acs.org/doi/10.1021/acs.organomet.0c00629.
■
sı
Revised file (PDF)
REFERENCES
■
(1) (a) Jang, W. J.; Lee, W. L.; Moon, J. H.; Lee, J. Y.; Yun, J. Org. Lett.
2016, 18, 1390−1393. (b) Jang, W. J.; Kang, B.-N.; Lee, J. H.; Choi, Y.
M.; Kim, C.-H.; Yun, J. Org. Biomol. Chem. 2019, 17, 5249−5252.
https://dx.doi.org/10.1021/acs.organomet.0c00629
© XXXX American Chemical Society
Organometallics XXXX, XXX, XXX−XXX
A

Organometallics
pubs.acs.org/Organometallics
Addition/Correction
a
Table 2. Hydroboration Substrate Scope
a
1
Yield determined via H NMR spectroscopy vs 2,4,6-trimethylben-
zaldehyde as an internal standard (IPr 1,3-bis(2,6-
=
b
diisopropylphenyl)imidazol-2-ylidene. 1.0 mol % catalyst loading.
c
Yield determined via 19F NMR spectroscopy vs 4-fluorobenzoic acid
d
as an internal standard. Trace amount of linear product observed by
GC-MS (<1%); not observed by H NMR spectroscopy. Isolated
e
1
f
yield. α,α,α-Trifluorotoluene used as the internal standard.
g
h
Branched product observed by GC-MS (<5%). Trace amount of
1
branched product observed by GC-MS (<1%); not observed by H
NMR spectroscopy. 47% of the branched product observed by H
i
1
j
1
NMR spectroscopy. 4% of branched product observed by H NMR
k
spectroscopy. 8% of branched product observed by 1H NMR
spectroscopy.
B
https://dx.doi.org/10.1021/acs.organomet.0c00629
Organometallics XXXX, XXX, XXX−XXX