Home / Publications / Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes

Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes

Liang Wang 1
Liang Wang
Yaoyao Wang 2
Yaoyao Wang
Yu Tao 1
Yu Tao
Nana Zhang 1
Nana Zhang
Shubai Li 1
Shubai Li
1 School of Chemical and Pharmaceutical Engineering, Changzhou Vocational Institute of Engineering, Changzhou, P.R. China
Published 2021-03-03
CommunicationVolume 31, Issue 2, 271-273
3
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Wang L. et al. Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 271-273.
GOST all authors (up to 50) Copy
Wang L., Wang Y., Tao Yu., Zhang N., Li S. Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 271-273.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2021.03.043
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.043
TI - Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes
T2 - Mendeleev Communications
AU - Wang, Liang
AU - Wang, Yaoyao
AU - Tao, Yu
AU - Zhang, Nana
AU - Li, Shubai
PY - 2021
DA - 2021/03/03
PB - Mendeleev Communications
SP - 271-273
IS - 2
VL - 31
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Wang,
author = {Liang Wang and Yaoyao Wang and Yu Tao and Nana Zhang and Shubai Li},
title = {Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.043},
number = {2},
pages = {271--273},
doi = {10.1016/j.mencom.2021.03.043}
}
MLA
Cite this
MLA Copy
Wang, Liang, et al. “Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes.” Mendeleev Communications, vol. 31, no. 2, Mar. 2021, pp. 271-273. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.043.

Keywords

aldehydes
arenecarboxylic acids
C–O cleavage
dimethyl dicarbonate
hydrosilanes
nickel catalysis

Abstract

Nickel-catalyzed reduction of (het)arenecarboxylic acids with hydrosilanes in the presence of dimethyl dicarbonate as the activator affords the corresponding aldehydes. The role of the activator is the conversion of the acids into their anhydrides undergoing C–O cleavage. The good yields were achieved in case of substrates bearing electron-donating and electron-neutral groups.

References

1.
10.1016/j.mencom.2021.03.043_bib0005
Johnstone
1991
4.
Selective switchable iron-catalyzed hydrosilylation of carboxylic acids
Misal Castro L.C., Li H., Sortais J., Darcel C.
Chemical Communications, 2012
5.
Selective reduction of carboxylic acids to aldehydes through manganese catalysed hydrosilylation
Zheng J., Chevance S., Darcel C., Sortais J.
Chemical Communications, 2013
6.
Selective Reduction of Carboxylic Acids to Aldehydes Catalyzed by B(C6F5)3
7.
Selective reduction of carboxylic acids to aldehydes with hydrosilane via photoredox catalysis
Zhang M., Li N., Tao X., Ruzi R., Yu S., Zhu C.
Chemical Communications, 2017
9.
Celebrating 100 years of the Rosenmund reaction
Iosub A.V., Wallentin C., Bergman J.
Nature Catalysis, 2018
11.
Direct Hydrogenation of Carboxylic Acids to Corresponding Aldehydes Catalyzed by Palladium Complexes
Nagayama K., Shimizu I., Yamamoto A.
Bulletin of the Chemical Society of Japan, 2001
12.
New Pd-catalyzed selective reduction of carboxylic acids to aldehydes
14.
A Mild and Efficient Catalytic Alkylative Monofunctionalization of Cyclic Anhydrides
Bercot E.A., Rovis T.
Journal of the American Chemical Society, 2001
16.
Nickel-catalyzed decarbonylative addition of anhydrides to alkynes.
Kajita Y., Kurahashi T., Matsubara S.
Journal of the American Chemical Society, 2008
17.
Decarbonylative Cycloaddition of Phthalic Anhydrides with Allenes
Ochi Y., Kurahashi T., Matsubara S.
Organic Letters, 2011
18.
Ni-Catalyzed Reductive Coupling of Alkyl Acids with Unactivated Tertiary Alkyl and Glycosyl Halides
Zhao C., Jia X., Wang X., Gong H.
Journal of the American Chemical Society, 2014
19.
Nickel-Catalyzed Desymmetrizing Cross-Electrophile Coupling of Cyclic Meso-Anhydrides
Lin T., Mi J., Song L., Gan J., Luo P., Mao J., Walsh P.J.
Organic Letters, 2018
22.
Direct Acylation of C(sp3 )−H Bonds Enabled by Nickel and Photoredox Catalysis
Joe C.L., Doyle A.G.
Angewandte Chemie - International Edition, 2016
23.
Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso-Anhydrides.
Stache E.E., Rovis T., Doyle A.G.
Angewandte Chemie - International Edition, 2017
24.
Synthesis of Reversed C‐Acyl Glycosides through Ni/Photoredox Dual Catalysis
Badir S.O., Dumoulin A., Matsui J.K., Molander G.A.
Angewandte Chemie - International Edition, 2018
25.
Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes
Iosub A.V., Moravčík Š., Wallentin C., Bergman J.
Organic Letters, 2019
26.
Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.
Qin T., Malins L.R., Edwards J.T., Merchant R.R., Novak A.J., Zhong J.Z., Mills R.B., Yan M., Yuan C., Eastgate M.D., Baran P.S.
Angewandte Chemie - International Edition, 2016
27.
Nickel-Catalyzed Reduction of Secondary and Tertiary Amides.
Simmons B.J., Hoffmann M., Hwang J., Jackl M.K., Garg N.K.
Organic Letters, 2017
28.
Ligand-Dependent Catalytic Cycle and Role of Styrene in Nickel-Catalyzed Anhydride Cross-Coupling:  Evidence for Turnover-Limiting Reductive Elimination
30.
Nickel-catalyzed Suzuki–Miyaura cross-couplings of aldehydes
Guo L., Srimontree W., Zhu C., Maity B., Liu X., Cavallo L., Rueping M.
Nature Communications, 2019