Palladium-Catalyzed Reaction of Propargylic Carbonates with Benzyne

Shengjun Ni; Wei Shu; Shengming Ma

doi:10.1055/s-0033-1339861

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(17): 2310-2314
DOI: 10.1055/s-0033-1339861

letter

Palladium-Catalyzed Reaction of Propargylic Carbonates with Benzyne

Shengjun Ni

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)62609305 eMail: masm@sioc.ac.cn

,

Wei Shu

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)62609305 eMail: masm@sioc.ac.cn

,

Shengming Ma*

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)62609305 eMail: masm@sioc.ac.cn

^bShanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. of China

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Abstract

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Abstract

Under the catalysis of palladium acetate, 1,2-allenylpalladium formed from propargylic carbonates may react with two molecules of benzyne to afford phenanthrene derivatives by cyclization and β-H elimination.

Key words

propargylic carbonates - allenylpalladium - phenanthrene derivatives - cyclization - β-H elimination

Volltext

Referenzen

References and Notes

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3 Tsuji J, Watanabe H, Minami I, Shimizu I. J. Am. Chem. Soc. 1985; 107: 2196

For reviews on Pd-catalyzed transformations of propargylic carbonates, see

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5a Ma S, Gu Z, Deng Y. Chem. Commun. 2006; 94
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6 Crystal Data for Compound 3f C₂₃H₁₈, MW = 294.14, monoclinic, space group P₂ (1), final R indices [I > 2σ(I)], R ₁ = 0.0472, wR ₂ = 0.1223, R indices (all data), R ₁ = 0.0593, wR ₂ = 0.1310, a = 6.2434(5) Å, b = 8.0127(7) Å, c = 21.1301(18) Å, α = 90^o, β = 90.262(2)^o, γ = 90^o, V = 1057.05(15) Å³, T = 293 (2) K, Z = 2, reflections collected/unique: 6377/4106 [R(int) = 0.0195], number of observations [>2σ(I)] 3264; parameter: 256. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Center (CCDC 941026).

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