Compound characterization data — Petrović et al., 2026

Nikola Petrović, Alberto Bonino, Sulekha Sharma, Cecilia Bottecchia, Dan Lehnherr, C. Oliver Kappe, Gabriele Laudadio. “The role of electrochemically reduced tungsten in deoxygenative reactions.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15001768/v2

WCl₆
Cyclic voltammetry (100 mV s⁻¹; glassy-carbon working electrode; platinum counter electrode; 0.1 M LiCl in NMP; 0.01 M analyte)	Two distinct reductive events between −1.2 V and −1.7 V vs Ag/AgCl; further reduction did not seem viable within this redox window; image data were not transcribed

WCl₆ and aldehydes
Cyclic voltammetry (100 mV s⁻¹; glassy-carbon working electrode; platinum counter electrode; 0.1 M LiCl in NMP; Ag/AgCl reference)	The WCl₆ and benzaldehyde (1a) reduction events overlapped; the 3-phenylpropanal (1u) reduction event did not overlap
Cyclic voltammetry of 10 mM WCl₆ with 0–50 mM benzaldehyde (1a)	Progressive current increment between −2.2 V and −1.1 V vs Ag/AgCl; the rest of the scanned potentials remained unaltered; image data were not transcribed

Electrolyzed WCl₆ solution
Cyclic voltammetry before and after heating	No clear evidence that WOCl₄ or WO₂Cl₂ were generated; image data were not transcribed

Cinnamaldehyde
Identifier	1aa
Cyclic voltammetry with and without WCl₆	The quasi-reversible reduction was partially suppressed when WCl₆ was added; image data were not transcribed

Freshly electrolyzed mixture with benzaldehyde
Identifier	1a; Int-A
LC–ESI-MS(−) (MeCN:0.1 % HCOOH in H₂O 80:20), [C₁₄H₁₂Cl₄O₂W]²⁻	m/z [M+Li⁺]⁻ found 543.1 (calculated 542.9)
LC–ESI-MS(−) (MeCN:0.1 % HCOOH in H₂O 80:20), [C₁₈H₁₈Cl₂N₂O₂W]	m/z [M+HCOO⁻]⁻ found 593.2 (calculated 593.0)

FT-IR standards
Samples	NMP; WCl₆; WOCl₄; WO₂Cl₂; benzaldehyde (1a); WCl₆ + benzaldehyde (1a); diol (3a); WCl₆ + diol (3a); stilbene (2a); WCl₆ + stilbene (2a)
FT-IR	Image data were not transcribed

Batch reaction mixture
FT-IR states	WCl₆ electrolysis; diol addition; after heating; image data were not transcribed

Real-time flow reaction mixture
FT-IR tracked wavenumbers	922, 983, 1114, 1645, 986, 933 cm⁻¹
FT-IR during electrolysis	The IR spectra showed the accumulation of an intermediate species while benzaldehyde was consumed
FT-IR after electrolysis	The intermediate was converted to the desired product, leading to the formation of W-oxo species
FT-IR assignment	The pattern of the peaks and the absence of water formation indicated the formation of WO₂L₂ species
FT-IR spectra and time profile	Image data were not transcribed

(E)-1,2-Diphenylethene
Identifier	2a
¹H NMR (300 MHz, CDCl₃)	δ 7.61–7.48 (m, 4H), 7.45–7.33 (m, 4H), 7.33–7.25 (m, 2H), 7.14 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 137.5, 128.8, 127.8, 126.7

(E)-1,2-Bis(4-fluorophenyl)ethene
Identifier	2b
¹H NMR (300 MHz, CDCl₃)	δ 7.52–7.41 (m, 4H), 7.11–7.00 (m, 4H), 6.98 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 162.5 (d, J = 247.3 Hz), 133.5 (d, J = 3.2 Hz), 128.1 (d, J = 8.1 Hz), 127.4 (d, J = 1.8 Hz), 115.8 (d, J = 21.7 Hz)
¹⁹F NMR (282 MHz, CDCl₃)	δ −113.59–−115.19 (m)

(E)-1,2-Bis(4-chlorophenyl)ethene
Identifier	2c
¹H NMR (300 MHz, CDCl₃)	7.46–7.39 (m, 4H), 7.37–7.27 (m, 4H), 7.02 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 135.6, 133.6, 129.1, 128.1, 127.8

(E)-1,2-Bis(4-bromophenyl)ethene
Identifier	2d
¹H NMR (300 MHz, CDCl₃)	δ 7.51–7.45 (m, 4H), 7.39–7.34 (m, 4H), 7.02 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 136.1, 132.0, 131.9, 128.3, 128.2, 121.8

(E)-1,2-Bis(4-iodophenyl)ethene
Identifier	2e
¹H NMR (300 MHz, CDCl₃)	δ 7.59–7.54 (m, 4H), 6.87–6.81 (m, 4H), 6.67 (s, 2H)

(E)-1,2-Bis(4-methoxyphenyl)ethene
Identifier	2f
¹H NMR (300 MHz, CDCl₃)	δ 7.50–7.35 (m, 4H), 6.95–6.84 (m, 6H), 3.83 (s, 6H)
¹³C NMR (75 MHz, CDCl₃)	δ 159.1, 130.6, 127.6, 126.3, 114.2, 55.5

(E)-1,2-Bis(4-(methylthio)phenyl)ethene
Identifier	2g
¹H NMR (300 MHz, CDCl₃)	δ 7.47–7.36 (m, 4H), 7.26–7.20 (m, 4H), 7.02 (s, 2H), 2.50 (s, 6H)
¹³C NMR (75 MHz, CDCl₃)	δ 137.9, 134.4, 127.6, 127.0, 126.9, 16.0

(E)-4,4′-(Ethene-1,2-diyl)dibenzonitrile
Identifier	2h
¹H NMR (300 MHz, CDCl₃)	δ 7.68 (d, J = 8.5 Hz, 4H), 7.61 (d, J = 8.5 Hz, 4H), 7.20 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 140.8, 132.8, 130.5, 127.4, 118.9, 111.8

(E)-1,2-Bis(4-vinylphenyl)ethene
Identifier	2i
¹H NMR (300 MHz, CDCl₃)	δ 7.53–7.44 (m, 4H), 7.44–7.37 (m, 4H), 7.10 (s, 2H), 6.72 (dd, J = 17.6, 10.9 Hz, 2H), 5.77 (dd, J = 17.6, 0.9 Hz, 2H), 5.25 (dd, J = 10.9, 0.9 Hz, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 137.1, 137.0, 136.6, 128.3, 126.8, 126.7, 113.9

(E)-4,4′-(Ethene-1,2-diyl)dibenzaldehyde
Identifier	2j
¹H NMR (300 MHz, CDCl₃)	δ 10.02 (s, 2H), 7.95–7.87 (m, 4H), 7.74–7.66 (m, 4H), 7.30 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 191.7, 142.6, 136.0, 130.8, 130.4, 127.5

(E)-1,1′-(Ethene-1,2-diylbis(4,1-phenylene))bis(ethan-1-one)
Identifier	2k
¹H NMR (300 MHz, CDCl₃)	δ 10.02 (s, 2H), 7.95–7.87 (m, 4H), 7.74–7.66 (m, 4H), 7.30 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 197.6, 141.4, 136.6, 130.3, 129.1, 127.0, 26.8

(E)-1,2-Bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene
Identifier	2l
¹H NMR (300 MHz, CDCl₃)	δ 7.80 (d, J = 8.1 Hz, 4H), 7.52 (d, J = 8.2 Hz, 4H), 7.18 (s, 2H), 1.35 (s, 24H)
¹³C NMR (75 MHz, CDCl₃)	δ 140.0, 135.3, 129.7, 126.0, 84.0, 25.0; (C-B) carbon signal not observed due to quadrupolar relaxation

(E)-1,2-Dimesitylethene
Identifier	2m
¹H NMR (300 MHz, CDCl₃)	δ 6.95 (s, 4H), 6.57 (s, 2H), 2.41 (s, 12H), 2.33 (s, 6H)
¹³C NMR (75 MHz, CDCl₃)	δ 136.3, 136.1, 134.9, 132.1, 128.8, 21.5, 21.1

(E)-1,2-Bis(5-bromo-2-fluorophenyl)ethene
Identifier	2n
¹H NMR (300 MHz, CDCl₃)	δ 7.73 (dd, J = 6.6, 2.5 Hz, 2H), 7.36 (ddd, J = 8.7, 4.5, 2.5 Hz, 2H), 7.23 (s, 2H), 6.98 (dd, J = 10.1, 8.7 Hz, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 161.3, 132.3 (d, J = 8.5 Hz), 130.0 (d, J = 3.5 Hz), 126.80 (d, J = 13.5 Hz), 123.4–122.6 (m), 117.8 (d, J = 23.8 Hz), 117.2 (d, J = 3.4 Hz)
¹⁹F NMR (282 MHz, CDCl₃)	δ −119.60 (ddd, J = 10.4, 6.6, 4.3 Hz)

(E)-1,2-Di-m-tolylethene
Identifier	2o
¹H NMR (300 MHz, CDCl₃)	δ 7.36 (d, J = 8.3 Hz, 4H), 7.30 (d, J = 7.4 Hz, 2H), 7.12 (d, J = 4.3 Hz, 4H), 2.42 (s, 6H)
¹³C NMR (75 MHz, CDCl₃)	δ 138.3, 137.5, 128.7, 128.7, 128.5, 127.3, 123.8, 21.6

(E)-1,2-Bis(2-(trifluoromethyl)phenyl)ethene
Identifier	2p
¹H NMR (300 MHz, CDCl₃)	δ 7.79 (d, J = 7.8 Hz, 2H), 7.69 (d, J = 9.2 Hz, 2H), 7.63–7.54 (m, 2H), 7.48–7.36 (m, 4H)
¹³C NMR (75 MHz, CDCl₃)	δ 136.1–136.0 (m), 132.3, 128.6, 127.8 (d, J = 24.1 Hz), 128.6–127.3 (m), 126.3, 126.1 (q, J = 5.7 Hz), 122.7
¹⁹F NMR (282 MHz, CDCl₃)	δ −59.26

(E)-1,2-Bis(2-allylphenyl)ethene
Identifier	2q
¹H NMR (300 MHz, CDCl₃)	δ 7.71–7.56 (m, 2H), 7.28 (ddd, J = 4.7, 3.2, 1.1 Hz, 4H), 7.25–7.17 (m, 4H), 6.04 (ddt, J = 17.1, 10.2, 6.2 Hz, 2H), 5.40–4.82 (m, 4H), 3.56 (dt, J = 6.1, 1.6 Hz, 4H)
¹³C NMR (75 MHz, CDCl₃)	δ 137.7, 137.1, 136.9, 130.0, 128.2, 127.9, 126.9, 126.1, 116.11, 37.9

(E)-1,2-Di(furan-2-yl)ethene
Identifier	2r
¹H NMR (300 MHz, DMSO-d₆)	δ 7.78–7.58 (m, 2H), 6.82 (s, 2H), 6.59–6.47 (m, 4H)
¹³C NMR (75 MHz, DMSO-d₆)	δ 152.2, 143.0, 114.5, 112.1, 109.5

(E)-1,2-Di(thiophen-3-yl)ethene
Identifier	2s
¹H NMR (300 MHz, DMSO-d₆)	δ 7.55 (dd, J = 5.0, 2.9 Hz, 2H), 7.49 (dd, J = 2.9, 1.3 Hz, 2H), 7.43 (dd, J = 5.0, 1.3 Hz, 2H), 7.10 (s, 2H)
¹³C NMR (75 MHz, DMSO-d₆)	δ 140.0, 126.9, 125.0, 122.9, 122.6

(E)-1,1,6,6-Tetraphenylhexa-1,3,5-triene
Identifier	2t
¹H NMR (300 MHz, CDCl₃)	δ 7.49–7.38 (m, 6H), 7.30–7.23 (m, 14H), 6.86–6.63 (m, 2H), 6.53 (dd, J = 7.6, 3.1 Hz, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 143.0, 142.2, 139.9, 132.7, 130.7, 128.6, 128.4, 128.3, 127.6, 127.6, 127.5

1,6-Diphenylhex-3-ene
Identifier	2u
E/Z ratio (NMR)	2.5:2
E/Z ratio (GC–MS)	3.5:1
¹H NMR (300 MHz, CDCl₃)	δ 7.35–7.23 (m, 4H), 7.18 (ddd, J = 8.0, 7.0, 1.5 Hz, 6H), 5.48 (td, J = 3.6, 1.8 Hz, 2H), 2.66 (dd, J = 9.0, 6.6 Hz, 4H), 2.30 (dtd, J = 7.7, 5.3, 2.5 Hz, 4H)
¹³C NMR (75 MHz, CDCl₃)	δ 142.2, 130.2, 129.6, 128.6, 128.4, 125.9, 125.9, 36.2, 36.0, 34.6

(E)-But-2-ene-2,3-diyldibenzene
Identifier	2v
¹H NMR (300 MHz, CDCl₃)	δ 7.12–7.05 (m, 4H), 7.05–7.00 (m, 2H), 7.00–6.91 (m, 4H), 2.17 (s, 6H)
¹³C NMR (75 MHz, CDCl₃)	δ 144.8, 133.0, 129.3, 127.7, 125.7, 21.6

9H,9′H-9,9′-Bifluorene
Identifier	2w
¹H NMR (300 MHz, CDCl₃)	δ 7.66 (dt, J = 7.6, 1.0 Hz, 4H), 7.30 (d, J = 7.5 Hz, 4H), 7.10 (t, J = 8.0 Hz, 4H), 6.97 (d, J = 7.6 Hz, 4H), 4.85 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 144.8, 141.7, 127.4, 126.9, 124.2, 119.8, 49.9

1,1,2,2-Tetraphenylethene
Identifier	2x
¹H NMR (300 MHz, CDCl₃)	δ 7.14–7.07 (m, 12H), 7.06–6.99 (m, 8H)
¹³C NMR (75 MHz, CDCl₃)	δ 143.9, 141.1, 131.5, 127.8, 126.5

Styrene
Identifier	2y
¹H NMR (300 MHz, CDCl₃)	δ 7.49–7.42 (m, 2H), 7.41–7.32 (m, 2H), 7.32–7.24 (m, 1H), 6.76 (dd, J = 17.6, 10.9 Hz, 1H), 5.79 (dd, J = 17.6, 0.9 Hz, 1H), 5.28 (dd, J = 10.9, 0.9 Hz, 1H)
¹³C NMR (75 MHz, CDCl₃)	δ 137.7, 137.0, 128.7, 127.9, 126.3, 113.9

(E)-1,2-Di(pyridin-4-yl)ethene
Identifier	2z
¹H NMR (300 MHz, CDCl₃)	δ 8.72–8.52 (m, 4H), 7.50–7.37 (m, 4H), 7.23 (s, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 150.5, 143.6, 130.7, 121.3

(E)-1,2-Diphenylethane
Identifier	2a′
¹H NMR (300 MHz, CDCl₃)	δ 7.35–7.28 (m, 4H), 7.25–7.18 (m, 6H), 2.95 (s, 4H)
¹³C NMR (75 MHz, CDCl₃)	δ 141.9, 128.6, 128.5, 126.1, 38.1

(1E,3E,5E)-1,6-Diphenylhexa-1,3,5-triene
Identifier	2aa
¹H NMR (300 MHz, CDCl₃)	δ 7.45–7.39 (m, 4H), 7.32 (ddd, J = 7.5, 6.6, 1.2 Hz, 4H), 7.25–7.19 (m, 2H), 6.89 (ddd, J = 15.5, 7.1, 3.1 Hz, 2H), 6.60 (d, J = 15.5 Hz, 2H), 6.55–6.47 (m, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 137.5, 133.7, 132.8, 129.3, 128.8, 127.7, 126.5

1,1′:4′,1″-Terphenyl
Identifier	4aa
¹H NMR (300 MHz, CDCl₃)	δ 7.70 (s, 4H), 7.69–7.62 (m, 4H), 7.53–7.43 (m, 4H), 7.42–7.34 (m, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 140.8, 140.3, 129.0, 127.6, 127.5, 127.2

4,4″-Difluoro-1,1′:4′,1″-terphenyl
Identifier	4ab
¹H NMR (300 MHz, CDCl₃)	δ 7.67–7.52 (m, 8H), 7.20–7.11 (m, 4H)
¹³C NMR (75 MHz, CDCl₃)	δ 162.7 (d, J = 246.7 Hz), 139.3, 136.9 (d, J = 3.3 Hz), 128.7 (d, J = 8.1 Hz), 127.6, 115.9 (d, J = 21.4 Hz)
¹⁹F NMR (282 MHz, CDCl₃)	δ −115.33–−115.70 (m)

4,4″-Dichloro-1,1′:4′,1″-terphenyl
Identifier	4ac
¹H NMR (300 MHz, CDCl₃)	δ 7.64 (s, 4H), 7.60–7.53 (m, 4H), 7.47–7.40 (m, 4H)
¹³C NMR (75 MHz, CDCl₃)	δ 139.4, 139.1, 133.7, 129.2, 128.4, 127.6

4,4″-Dibromo-1,1′:4′,1″-terphenyl
Identifier	4ad
¹H NMR (300 MHz, CDCl₃)	δ 7.63 (s, 4H), 7.61–7.56 (m, 4H), 7.52–7.47 (m, 4H)

4,4″-Diiodo-1,1′:4′,1″-terphenyl
Identifier	4ae
¹H NMR (300 MHz, CDCl₃)	δ 7.82–7.75 (m, 4H), 7.63 (s, 4H), 7.40–7.34 (m, 4H)

4,4″-Dimethyl-1,1′:4′,1″-terphenyl
Identifier	4af
¹H NMR (300 MHz, CDCl₃)	δ 7.72–7.62 (m, 4H), 7.61–7.52 (m, 4H), 7.30 (d, J = 6.7 Hz, 4H), 2.43 (s, 6H)
¹³C NMR (75 MHz, CDCl₃)	δ 139.9, 138.0, 137.2, 129.7, 127.4, 127.0, 21.3

4,4″-Dimethoxy-1,1′:4′,1″-terphenyl
Identifier	4ag
¹H NMR (300 MHz, CDCl₃)	δ 7.61 (s, 4H), 7.60–7.53 (m, 4H), 7.05–6.94 (m, 4H), 3.86 (s, 6H)
¹³C NMR (75 MHz, CDCl₃)	δ 159.3, 139.3, 133.5, 128.2, 127.2, 114.4, 55.5

[1,1′:4′,1″-Terphenyl]-4,4″-dicarbaldehyde
Identifier	4ah
¹H NMR (300 MHz, CDCl₃)	δ 10.08 (s, 2H), 8.04–7.95 (m, 4H), 7.86–7.78 (m, 4H), 7.77 (s, 4H)
¹³C NMR (75 MHz, CDCl₃)	δ 191.9, 146.3, 139.8, 135.5, 130.4, 128.0, 127.6

4,4″-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′:4′,1″-terphenyl
Identifier	4ai
¹H NMR (300 MHz, CDCl₃)	δ 7.95–7.85 (m, 41H), 7.71 (s, 4H), 7.69–7.63 (m, 4H), 1.37 (s, 24H)
¹³C NMR (75 MHz, CDCl₃)	δ 143.4, 140.3, 135.5, 127.7, 126.5, 84.0, 25.0; (C-B) carbon signal not observed due to quadrupolar relaxation

4,4″-Bis(trimethylsilyl)-1,1′:4′,1″-terphenyl
Identifier	4aj
¹H NMR (300 MHz, CDCl₃)	δ 7.68 (s, 4H), 7.63 (d, J = 0.6 Hz, 8H), 0.31 (s, 18H)
¹³C NMR (75 MHz, CDCl₃)	δ 141.2, 140.3, 139.5, 134.0, 127.7, 126.5, −0.9

1,4-Di(pyridin-3-yl)benzene
Identifier	4ak
¹H NMR (300 MHz, CDCl₃)	δ 8.92 (s, 2H), 8.64 (d, J = 3.6 Hz, 2H), 7.97 (dt, J = 7.9, 2.0 Hz, 2H), 7.72 (s, 4H), 7.44 (dd, J = 7.9, 4.9 Hz, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 148.5, 148.0, 137.7, 136.2, 134.8, 128.0, 124.0

1,4-Di(furan-2-yl)benzene
Identifier	4al
¹H NMR (300 MHz, CDCl₃)	δ 7.69 (s, 4H), 7.48 (dd, J = 1.9, 0.7 Hz, 2H), 6.67 (dd, J = 3.4, 0.8 Hz, 2H), 6.49 (dd, J = 3.4, 1.8 Hz, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 153.9, 142.3, 129.8, 124.2, 111.9, 105.3

1,4-Di(thiophen-2-yl)benzene
Identifier	4am
¹H NMR (300 MHz, CDCl₃)	δ 7.63 (s, 4H), 7.35 (dd, J = 3.6, 1.2 Hz, 2H), 7.30 (dd, J = 5.1, 1.2 Hz, 2H), 7.10 (dd, J = 5.1, 3.6 Hz, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 144.0, 133.6, 128.3, 126.4, 125.0, 123.2

Benzo[1,2-b:4,5-b′]dithiophene
Identifier	4an
¹H NMR (300 MHz, CDCl₃)	δ 8.36–8.27 (m, 2H), 7.47 (d, J = 5.5 Hz, 2H), 7.37 (dd, J = 5.5, 0.5 Hz, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 137.6, 137.2, 127.2, 123.1, 117.0

(E)-4-Phenyl-5-styryltetrahydrofuran-2-ol
Identifier	5
¹H NMR (300 MHz, CDCl₃)	δ 7.49–7.38 (m, 6H), 7.30–7.23 (m, 14H), 6.86–6.63 (m, 2H), 6.53 (dd, J = 7.6, 3.1 Hz, 2H)
¹³C NMR (75 MHz, CDCl₃)	δ 139.5, 136.9, 131.6, 128.6, 128.6, 128.5, 127.6, 127.5, 126.9, 126.6, 98.4, 82.1, 47.5, 39.7

Compounds 2a–2aa, 4aa–4an and 5
NMR spectra	Image data were not transcribed