Tetrahedron Letters

An expedient synthesis of 3-substituted indoles via reductive alkylation with ketones

JR Rizzo, CA Alt, TY Zhang

Index: Rizzo, John R.; Alt, Charles A.; Zhang, Tony Y. Tetrahedron Letters, 2008 , vol. 49, # 48 p. 6749 - 6751

Full Text: HTML

Citation Number: 16

Abstract

3-Alkylindoles were prepared in one step from indoles and ketones via a convenient reductive alkylation procedure using triethylsilane and trichloroacetic acid. Under this particular condition, unsubstituted indoles could be tolerated to afford good yields of 3-sec- alkylation products.

Related Articles:

Direct benzylation and allylic alkylation in high-temperature water without added catalysts

[Hirashita, Tsunehisa; Kuwahara, Sho; Okochi, Sota; Tsuji, Makoto; Araki, Shuki Tetrahedron Letters, 2010 , vol. 51, # 14 p. 1847 - 1851]

Discovery of the Macrocycle 11-(2-Pyrrolidin-1-yl-ethoxy)-14, 19-dioxa-5, 7, 26-triaza-tetracyclo [19.3. 1.1 (2, 6). 1 (8, 12)] heptacosa-1 (25), 2 (26), 3, 5, 8, 10, 12 (27), …

[Koehling, Petra; Schmidt, Axel M.; Eilbracht, Peter Organic Letters, 2003 , vol. 5, # 18 p. 3213 - 3216]

Rapid and General Protocol towards Catalyst??Free Friedel–Crafts C??Alkylation of Indoles in Water Assisted by Microwave Irradiation

[De Rosa, Margherita; Soriente, Annunziata European Journal of Organic Chemistry, 2010 , # 6 p. 1029 - 1032]

More Articles...