Generation of Aryl Grignard Reagents from Arene Chromium Tricarbonyl Complexes by Mg(TMP)2·2LiCl and Their Application to Murahashi Coupling

Yuichi Momoi; Kentaro Okano; Hidetoshi Tokuyama

doi:10.1055/s-0034-1379205

Synlett, Table of Contents

Synlett 2014; 25(17): 2503-2507
DOI: 10.1055/s-0034-1379205

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Generation of Aryl Grignard Reagents from Arene Chromium Tricarbonyl Complexes by Mg(TMP)₂·2LiCl and Their Application to Murahashi Coupling

Yuichi Momoi

Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, 980-8578 Sendai, Japan Fax: +81(22)7956877 Email: tokuyama@mail.pharm.tohoku.ac.jp

,

Kentaro Okano

Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, 980-8578 Sendai, Japan Fax: +81(22)7956877 Email: tokuyama@mail.pharm.tohoku.ac.jp

,

Hidetoshi Tokuyama*

Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, 980-8578 Sendai, Japan Fax: +81(22)7956877 Email: tokuyama@mail.pharm.tohoku.ac.jp

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Abstract

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Abstract

A mild and straightforward synthesis of biaryls is described that is performed through direct arylation of the C–H bond of (arene)Cr(CO)₃ upon deprotonation with Mg(2,2,6,6-tetramethylpiperazide)₂·2LiCl and subsequent palladium-catalyzed cross-coupling reaction.

Key words

chromium - copper - cross-coupling - magnesium - palladium

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References

References and Notes

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22 Synthesis of (Biaryl)Cr(CO)₃ 9a: A 30 mL two-necked round-bottomed flask equipped with a magnetic stirring bar was charged with 7a (249 mg, 1.02 mmol) and THF (1.0 mL). To the solution was added freshly prepared Mg(TMP)₂·2LiCl (0.10 M in THF, 11 mL, 1.1 mmol) dropwise over 5 min at 0 °C. The resulting mixture was stirred at 0 °C for 1 h. To the yellow solution was added CuI (114 mg, 0.60 mmol) portionwise at 0 °C. After the mixture was stirred at 0 °C for 1 h, methyl p-iodobenzoate (13a; 524 mg, 2.0 mmol) and Pd(PPh₃)₄ (117.9 mg, 102 μmol) were added and the reaction mixture was stirred at r.t. for 1 h. The reaction was quenched with sat. aq NH₄Cl, and the mixture was stirred for 10 min. The resulting mixture was filtered through a Celite pad and the filtrate was extracted with Et₂O. The combined organic extracts were washed with brine, dried over anhydrous Na₂SO₄, and filtered. The filtrate was concentrated under reduced pressure to give a crude black solid, which was purified by silica gel column chromatography (EtOAc–hexanes, 1:3 to 1:1) to provide (biaryl)Cr(CO)₃ 9a (353 mg, 0.915 mmol, 90%) as a dark-red solid. IR (neat): 1955, 1862 (CO stretch), 1715, 1279, 1251, 1111, 825, 773, 662 cm^–1; ¹H NMR (400 MHz, CDCl₃): δ = 8.04 (d, J = 8.0 Hz, 2 H), 7.60 (d, J = 8.0 Hz, 2 H), 5.75 (d, J = 6.8 Hz, 1 H), 5.63 (dd, J = 6.8, 6.8 Hz, 1 H), 5.13 (d, J = 6.8 Hz, 1 H), 4.98 (dd, J = 6.8, 6.8 Hz, 1 H), 3.93 (s, 3 H), 3.76 (s, 3 H); ¹³C NMR (100 MHz, CDCl₃): δ = 232.3, 166.3, 141.1, 138.8, 130.1, 129.7, 129.0, 99.7, 97.7, 94.2, 84.2, 72.9, 55.7, 51.9; MS (EI): m/z = 378 [M]⁺; HRMS (EI): m/z [M]⁺ calcd for C₁₈H₁₄CrO₆: 378.0196; found: 378.0184.