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Synlett 2014; 25(17): 2434-2437
DOI: 10.1055/s-0034-1379181
DOI: 10.1055/s-0034-1379181
letter
Diastereoselective Oxidative Cross-Coupling Reactions of Chiral Alkylbenzenes with Arenes and Silyl Nucleophiles
Weitere Informationen
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).
Key words
carbocation - diastereoselectivity - electrophilic aromatic substitution - oxidation - stereoselective synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083. Included are procedures and analytical data for all new compounds and crystal structure data.
- Supporting Information
-
References and Notes
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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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Reviews:
Reviews:
Selected examples:
Selected examples:
Selected examples:
For additional examples for FeCl2-catalyzed benzylic DDQ oxidation, see refs. 4b,6f and:
For mechanistic studies towards the benzylic DDQ oxidation, see: