Synlett 2014; 25(17): 2434-2437
DOI: 10.1055/s-0034-1379181
letter
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Oxidative Cross-Coupling Reactions of Chiral Alkylbenzenes with Arenes and Silyl Nucleophiles

Dominik Nitsch
Department Chemie and Catalysis Research Center (CRC), Technische Universität München, 85747 Garching, Germany   Fax: +49(89)28913315   eMail: thorsten.bach@ch.tum.de
,
Alexander Pöthig
Department Chemie and Catalysis Research Center (CRC), Technische Universität München, 85747 Garching, Germany   Fax: +49(89)28913315   eMail: thorsten.bach@ch.tum.de
,
Thorsten Bach*
Department Chemie and Catalysis Research Center (CRC), Technische Universität München, 85747 Garching, Germany   Fax: +49(89)28913315   eMail: thorsten.bach@ch.tum.de
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Publikationsverlauf

Received: 27. August 2014

Accepted: 28. August 2014

Publikationsdatum:
18. September 2014 (online)


Abstract

Chiral di- and trimethoxysubstituted alkylbenzenes underwent oxidative cross-dehydrogenative coupling reactions with arenes and related oxidative coupling reactions with silyl nucleophiles in moderate to good yields (41–99%) and with significant diastereoselectivities (dr = 71:29 to >95:5).

Supporting Information

 
  • References and Notes

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  • 10 For the preparation of starting materials, see the Supporting Informaton. All chiral compounds in this manuscript were used or obtained as racemic mixtures. The relative configuration of racemates is displayed by straight bonds (bold or hashed), following a convention suggested previously: Maehr H. J. Chem. Ed. 1985; 62: 114

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  • 12 General Experimental Procedure for FeCl2-Catalyzed, DDQ-Mediated Cross-Coupling Reactions To a solution of the substrate 3 (200 μmol, 1.00 equiv), nucleophile (800 μmol, 4.00 equiv), FeCl2 (40 μmol, 0.20 equiv), and MeNO2 (c 100 mM) in a flame-dried flask was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (260 μmol, 1.30 equiv) at r.t. After 1 h the solvent was removed under reduced pressure, and the crude mixture was purified by flash column chromatography (silica gel; pentane–EtOAc, 40:1) to afford the product.
  • 13 General Experimental Procedure for DDQ-Mediated Cross-Coupling Reactions To a solution of the substrate 5 (200 μmol, 1.00 equiv), nucleophile (800 μmol, 4.00 equiv), and MeNO2 (c 100 mM) in a flame-dried flask was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (260 μmol, 1.30 equiv) at r.t. After 1 h the solvent was removed under reduced pressure, and the crude mixture was purified by flash column chromatography (silica gel; pentane–EtOAc, 40:1) to afford the product.
  • 14 Crystal Structure of 6f Colorless plates, C24H34O5, crystal dimensions 0.12 × 0.13 × 0.13 mm; M r = 402.51; monoclinic, space group P 21/n, a = 13.558(3), b = 11.365(2), c = 15.410(3) Å, β = 112.740(6)°, V = 2189.9(7) Å3, Z = 4, λ(Mo Kα) = 0.71073 Å, μ = 0.084 mm–1, ρ calcd = 1.221 g cm–3, T = 123(2) K, F (000) = 872, angle range θ = 1.70–23.26°; collected data: 16558; independent data [I o > 2σ(I o)/all data/R int]: 1913/3089/0.1067; data/restraints/parameter: 3089/0/272; R1 [I o > 2σ(I o)/all data]: 0.0816/0.1330; wR2 [I o > 2σ(I o)/ all data]: 0.1855/0.2073; GOF = 1.049; Δρ max/min: 0.861/–0.271 eÅ–3. CCDC-1016616. For more details, see the Supporting Information.

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