Palladium-Catalyzed Reaction of Propargylic Carbonates with Benzyne

Shengjun Ni; Wei Shu; Shengming Ma

doi:10.1055/s-0033-1339861

Synlett, Table of Contents

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

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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

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References

References and Notes

1a Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
1b Gellert E. J. Nat. Prod. 1982; 45: 50
1c Li ZG, Jin Z, Huang RQ. Synthesis 2001; 2365

For recent reports on synthesis of phenanthrene, see:

2a Matsumoto A, Ilies L, Nakamura E. J. Am. Chem. Soc. 2011; 133: 6557
2b Wang C, Rakshit S, Glorius F. J. Am. Chem. Soc. 2010; 132: 14006
2c Neo AG, López C, Romero V, Antelo B, Delamano J, Pérez A, Fernández D, Almeida JF, Castedo L, Tojo G. J. Org. Chem. 2010; 75: 6764
2d Yoshikawa E, Yamamoto Y. Angew. Chem. Int. Ed. 2000; 39: 173
2e Yoshikawa E, Radhakrishnan KV, Yamamoto Y. J. Am. Chem. Soc. 2000; 122: 7280
2f Liu Z, Larock RC. Angew. Chem. Int. Ed. 2007; 46: 2535
2g Peña D, Pérez D, Guitián E, Castedo L. J. Am. Chem. Soc. 1999; 121: 5827

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

4a Tsuji J, Mandai T. Angew. Chem., Int. Ed. Engl. 1995; 34: 2589
4b Guo L, Duan X, Liang Y. Acc. Chem. Res. 2011; 44: 111 ; and references cited therein

5a Ma S, Gu Z, Deng Y. Chem. Commun. 2006; 94
5b Shu W, Jia G, Ma S. Org. Lett. 2009; 11: 117
5c Shu W, Ma S. Tetrahedron 2010; 66: 2869
5d Chen G, Zhang Y, Fu C, Ma S. Tetrahedron 2011; 67: 2332
5e Ye J, Li S, Ma S. Org. Lett. 2012; 14: 2312

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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