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Volumn , Issue 1, 2009, Pages 85-88

Electroreductive generation of recyclable organic reductant from N,N′-dioctyl-4,4′-bipyridinium and Pd-catalyzed reductive coupling of aryl halides

(4) Kuroboshi, Manabu a Kobayashi, Ryoto a Nakagawa, Takayuki a Tanaka, Hideo a

a OKAYAMA UNIVERSITY (Japan)

Author keywords

Coupling; Electron transfer; Halides; Palladium; Reductions

Indexed keywords

EID: 62349132854 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-2008-1087386 Document Type: Article

Times cited : (9)

References (37)

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- Purity of [C8V2, Tf2N, 2 was confirmed by 1H NMR, 13C NMR, IR, and elemental analysis. 1H NMR (200 MHz, CD2Cl2, δ, 0.8-1.0 (m, 6 H, 1.20-1.50 (m, 20 H, 1.90-2.20 (m, 4 H, 4.64 (t, J, 7.6 Hz, 4 H, 8.46 (d, J, 6.9 Hz, 4 H, 8.93 (d, J, 6.9 Hz, 4 H, 13C NMR (50 MHz, CD2Cl2, δ, 13.41, 22.16, 25.59, 28.41, 28.48, 31.01, 31.21, 62.57, 119.28 (q, J, 319.1 Hz, 127.03, 144.96, 149.50. IR KBr, 3136, 3104, 3074, 2952, 2929, 2861, 1644, 1347, 1203, 1133, 1058 cm-1. Anal. Calcd for C 30H42F12N4O8S 4: C, 38.21; H, 4.49; N, 5.94. Found: C, 38.28; H, 4.57; N, 5.93, C8V2, Tf2N-]2 was dried in vacuo at 100°C overnight and used without further purification
- 2 was dried in vacuo at 100°C overnight and used without further purification.

32
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- In a cathodic compartment of a divided cell was placed a THF (3 mL) solution of [C8V2, Tf2N, 2 (1 mmol, Bu4N, Tf2N, 2 mmol, and a Pt (1 x 1.5 cm2) cathode. In an anodic compartment was placed a THF (3 mL) solution of [Bu4N, Tf 2N, 2 mmol) and a Mg anode. A constant current (25 mA) was applied at r.t. until 2 F/mol [C8V2, Tf 2N-]2 of electricity was passed. The resulting dark blue solution in cathodic cell was added to a mixture of 1a (0.5 mmol) and a catalytic amount of PdCl2(PhCN)2 (0.025 mmol) by means of cannulation. The whole mixture was stirred for 30 h at 60°C. Usual workup and purification by column chromatography (SiO2) gave 2a 0.227 mmol, 91
- 2) gave 2a (0.227 mmol, 91%).

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- 2 did not promote the coupling, and the starting aryl bromides were recovered quantitatively.

35
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- 2 (0.025 mmol) to give 2a and 1a in 59% and 32% yield, respectively.
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- 2 (0.025 mmol), and THF (3 mL). A Mg anode and a Pt cathode were immersed in the solution, and a constant current (5 mA) was supplied at 60°C until 2 F/mol-1a of electricity was passed.
- 2 (0.025 mmol), and THF (3 mL). A Mg anode and a Pt cathode were immersed in the solution, and a constant current (5 mA) was supplied at 60°C until 2 F/mol-1a of electricity was passed.

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