American Chemical Society (ACS)
Organic Letters
,  volume 24 ,  issue 19 ,  pages 3499-3503

Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation?

Publication type: Journal Article
Publication date: 2022-05-06
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
In 2003, Martı́n et al. reported a green alcohol oxidation with FeBr3(cat.)/H2O2 and proposed a high-valent iron species (HIS) responsible for the alcohol oxidation. Reinvestigating this FeBr3(cat.)/H2O2 method led us to propose a different mechanism that involves a reactive brominating species (RBS) for the oxidation of alcohols. The evidence to support this RBS-based mechanism includes (1) our recent findings of in situ-generated RBS from the related FeBr2/H2O2 or CeBr3/H2O2 systems, (2) our results of a series of controlled experiments, and (3) some related RBS-based precedents (NBS, NBA, or Br2) showing similar high oxidation selectivity of secondary over primary alcohols. These studies enable us to discover that a RBS from CeBr3/H2O2 is much more efficient for the oxidation of secondary and benzylic alcohols, which represents a new green protocol for selective oxidation of alcohols to carbonyls.
Found 
Found 

Top-30

Journals

1
2
3
4
5
Journal of Organic Chemistry
Journal of Organic Chemistry, 5, 26.32%
Journal of Organic Chemistry
5 publications, 26.32%
Tetrahedron
Tetrahedron, 3, 15.79%
Tetrahedron
3 publications, 15.79%
Green Chemistry
Green Chemistry, 2, 10.53%
Green Chemistry
2 publications, 10.53%
Chem Catalysis
Chem Catalysis, 1, 5.26%
Chem Catalysis
1 publication, 5.26%
Tetrahedron Letters
Tetrahedron Letters, 1, 5.26%
Tetrahedron Letters
1 publication, 5.26%
Mendeleev Communications, 1, 5.26%
Mendeleev Communications
1 publication, 5.26%
Molecules
Molecules, 1, 5.26%
Molecules
1 publication, 5.26%
Accounts of Chemical Research
Accounts of Chemical Research, 1, 5.26%
Accounts of Chemical Research
1 publication, 5.26%
ChemCatChem
ChemCatChem, 1, 5.26%
ChemCatChem
1 publication, 5.26%
RSC Sustainability
RSC Sustainability, 1, 5.26%
RSC Sustainability
1 publication, 5.26%
Organic and Biomolecular Chemistry
Organic and Biomolecular Chemistry, 1, 5.26%
Organic and Biomolecular Chemistry
1 publication, 5.26%
Journal of Chemical Education
Journal of Chemical Education, 1, 5.26%
Journal of Chemical Education
1 publication, 5.26%
1
2
3
4
5

Publishers

1
2
3
4
5
6
7
American Chemical Society (ACS)
American Chemical Society (ACS), 7, 36.84%
American Chemical Society (ACS)
7 publications, 36.84%
Elsevier
Elsevier, 5, 26.32%
Elsevier
5 publications, 26.32%
Royal Society of Chemistry (RSC)
Royal Society of Chemistry (RSC), 4, 21.05%
Royal Society of Chemistry (RSC)
4 publications, 21.05%
OOO Zhurnal "Mendeleevskie Soobshcheniya", 1, 5.26%
OOO Zhurnal "Mendeleevskie Soobshcheniya"
1 publication, 5.26%
MDPI
MDPI, 1, 5.26%
MDPI
1 publication, 5.26%
Wiley
Wiley, 1, 5.26%
Wiley
1 publication, 5.26%
1
2
3
4
5
6
7
  • We do not take into account publications without a DOI.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
19
Share
Cite this
GOST |
Cite this
GOST Copy
He C. et al. Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation? // Organic Letters. 2022. Vol. 24. No. 19. pp. 3499-3503.
GOST all authors (up to 50) Copy
He C., Ma F., Zhang W., Tong R. Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation? // Organic Letters. 2022. Vol. 24. No. 19. pp. 3499-3503.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.2c01133
UR - https://doi.org/10.1021/acs.orglett.2c01133
TI - Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation?
T2 - Organic Letters
AU - He, Chenxi
AU - Ma, Foqing
AU - Zhang, Wei
AU - Tong, Rong-Biao
PY - 2022
DA - 2022/05/06
PB - American Chemical Society (ACS)
SP - 3499-3503
IS - 19
VL - 24
PMID - 35522028
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2022_He,
author = {Chenxi He and Foqing Ma and Wei Zhang and Rong-Biao Tong},
title = {Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation?},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.orglett.2c01133},
number = {19},
pages = {3499--3503},
doi = {10.1021/acs.orglett.2c01133}
}
MLA
Cite this
MLA Copy
He, Chenxi, et al. “Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation?.” Organic Letters, vol. 24, no. 19, May. 2022, pp. 3499-3503. https://doi.org/10.1021/acs.orglett.2c01133.