1,4-Reduction of α,β-unsaturated ketones catalyzed by tetraarylhydrophosphoranes
Data files
Sep 25, 2025 version files 53.42 MB
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FIDdata_rev.zip
53.41 MB
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README.md
5.04 KB
Abstract
We demonstrate that a pentavalent phosphorous compound, tetraarylhydrophosphorane, is capable of catalyzing 1,4-reduction of α,β-unsaturated ketones in the presence of pinacolborane. The structure and properties of tetraarylhydrophosphorane and its participation in the chemoselective 1,4-reduction were elucidated through both experimental and theoretical approaches.
Description of the data and file structure
The uploaded zip file contains primary nuclear magnetic resonance (NMR) files for compounds P2, PH2, 1b-1w, 1y, 2a-2y, 3a, 4a, 5a, and 5a’ (https://pubs.acs.org/doi/10.1021/acs.orglett.5c02773). These compounds are classified into the “Catalyst”, “StartingMaterial”, and "Product" folders. The detailed contents of each folder are provided in the section below. Each compound folder contains ¹H NMR and ¹³C NMR data; for some compounds, ¹⁹F NMR and ³¹P NMR data are also included. The filenames follow the format “CompoundName_Nuclear.”
The NMR data are stored in one of the following formats:
• “.jdf” (JEOL NMR instrument)
• A single folder containing “fid” (the main data file) and auxiliary files (Bruker NMR instrument)
To view the NMR spectrum, you need to give the ".jdf" file or the entire folder of files (e.g. FIDdata/StartingMaterial/1b/1b_H/) to the software (see "Code/Software" section). The software will use the fid file inside the file/folder and the associated files to generate the spectrum.
The full name of the compounds represented by the compound number
Catalyst folder
P2: 5,5-Diphenyl-5H-benzo[b]phosphindol-5-ium trifluoromethanesulfonate
PH2: (2,2’-Biphenylylene)diphenylhydrophosphorane
StartingMaterial folder
1b: (E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-one
1c: (E)-3-(4-(Cyclopropylmethoxy)phenyl)-1-phenylprop-2-en-1-one
1d: (E)-3-(4-Bromophenyl)-1-phenylprop-2-en-1-one
1e: (E)-1-Phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
1f: (E)-3-(2,6-Difluorophenyl)-1-phenylprop-2-en-1-one
1g: (E)-4-(3-Oxo-3-phenylprop-1-en-1-yl)benzonitrile
1h: (E)-3-(4-Nitrophenyl)-1-phenylprop-2-en-1-one
1i: (E)-3-(4-Acetylphenyl)-1-phenylprop-2-en-1-one
1j: Methyl (E)-4-(3-oxo-3-phenylprop-1-en-1-yl)benzoate
1k: (E)-3-(4-(Pent-1-yn-1-yl)phenyl)-1-phenylprop-2-en-1-one
1l: (E)-3-(Naphthalen-2-yl)-1-phenylprop-2-en-1-one
1m: (E)-1-Phenyl-3-(1-tosyl-1H-indol-5-yl)prop-2-en-1-one
1n: (E)-3-Ferrocenyl-1-phenylprop-2-en-1-one
1o: (E)-1-(4-Iodophenyl)-3-phenylprop-2-en-1-one
1p: (E)-1-(Benzo[d][1,3]dioxol-5-yl)-3-phenylprop-2-en-1-one
1q: (E)-1-(2,4-Dimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one
1r: (E)-3-Phenyl-1-(Thiophen-3-yl)prop-2-en-1-one
1s: (2E,2’E)-3,3’-(1,4-Phenylene)bis(1-phenylprop-2-en-1-one)
1t: (E)-1-Phenylhex-2-en-1-one
1u: (E)-4,4,4-Trifluoro-1-phenylbut-2-en-1-one
1v: (E)-4,4-Dimethyl-1-phenylpent-1-en-3-one
1w: (E)-1-Phenyloct-4-en-3-one
1y: (E)-1,7-Diphenylhept-2-ene-1,7-dione
Product folder
2a: 1,3-Diphenylpropan-1-one
2b: 3-(4-Methoxyphenyl)-1-phenylpropan-1-one
2c: 3-(4-(Cyclopropylmethoxy)phenyl)-1-phenylpropan-1-one
2d: 3-(4-Bromophenyl)-1-phenylpropan-1-one
2e: 1-Phenyl-3-(4-(trifluoromethyl)phenyl)propan-1-one
2f: 3-(2,6-Difluorophenyl)-1-phenylpropan-1-one
2g: 4-(3-Oxo-3-phenylpropyl)benzonitrile
2h: 3-(4-Nitrophenyl)-1-phenylpropan-1-one
2i: 3-(4-Acetylphenyl)-1-phenylpropan-1-one
2j: Methyl 4-(3-oxo-3-phenylpropyl)benzoate
2k: 3-(4-(Pent-1-yn-1-yl)phenyl)-1-phenylpropan-1-one
2l: 3-(Naphthalen-2-yl)-1-phenylpropan-1-one
2m: 1-Phenyl-3-(1-tosyl-1H-indol-3-yl)propan-1-one
2n: 3-Ferrocenyl-1-phenylpropan-1-one
2o: 1-(4-Iodophenyl)-3-phenylpropan-1-one
2p: 1-(Benzo[d][1,3]dioxol-5-yl)-3-phenylpropan-1-one
2q: 1-(2,4-Dimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one
2r: 3-Phenyl-1-(thiophen-3-yl)propan-1-one
2s: 3,3'-(1,4-Phenylene)bis(1-phenylpropan-1-one)
2t: 1-Phenylhexan-1-one
2u: 4,4,4-Trifluoro-1-phenylbutan-1-one
2v: 4,4-Dimethyl-1-phenylpentan-3-one
2w: 1-Phenyloctan-3-one
2x: 2-Pentylcyclopentan-1-one
2y: ((1R**,2S**)-2-Hydroxy-2-phenylcyclohexyl)(phenyl)methanone
3a: (E)-1,3-Diphenylprop-2-en-1-ol
4a: 2-Benzyl-2-bromoacetophenone
5a: (2R,3S)-2-Benzyl-3-cyclohexyl-3-hydroxy-1-phenylpropan-1-one
5a': (2R,3R)-2-Benzyl-3-cyclohexyl-3-hydroxy-1-phenylpropan-1-one
Sharing/Access information
Compound structures and their NMR data are available as images in the Supporting Information.
Code/Software
NMR data can be processed by various softwares, such as NMRium (https://app.nmrium.com/), MestReNova (https://mestrelab.com/software/mnova/), iNMR (free demo can display FID data) (https://www.inmr.net/), and JEOL Delta (https://www.jeol.com/products/scientific/nmr_software/Delta5.php).
They are collected through data acquisition on the NMR spectrometers.