Bismuth Salts in Catalytic Alkylation Reactions

作者: Magnus Rueping , Boris J. Nachtsheim

DOI: 10.1007/128_2011_191

关键词:

摘要: Alkylation reactions utilizing nontoxic Lewis acid catalysts and "green" alkylating reagents are of high interest due to the continuous need for environmentally benign C-C C-X bond formation. This article shows recent advances in Bi(III)-catalyzed alkylations arenes, 2,4-pentanediones various oxygen- nitrogen-containing nucleophiles. Instead toxic alkyl halides, electrophilic components these transformations were benzyl propargyl alcohols as well substrates with activated double bonds such styrenes. The fact that Bi(III) salts capable activating both σ- π-donors highlights their unique character versatile catalytic alkylation reactions. In addition, less cheaper than other acids have been described similar transformations.

参考文章(86)
Tao Pei, Ross A. Widenhoefer, Palladium-catalyzed cyclization of alkenyl β-keto esters in the presence of chlorotrimethylsilane Chemical Communications. pp. 650- 651 ,(2002) , 10.1039/B111644D
Thierry Ollevier, Etienne Nadeau, Valerie Desyroy, Bismuth(III) Trifluoromethanesulfonate e-EROS Encyclopedia of Reagents for Organic Synthesis. ,(2009) , 10.1002/047084289X.RN00959
Hongbo Qin, Noriyuki Yamagiwa, Shigeki Matsunaga, Masakatsu Shibasaki, Bismuth-Catalyzed Intermolecular Hydroamination of 1,3-Dienes with Carbamates, Sulfonamides, and Carboxamides Journal of the American Chemical Society. ,vol. 128, pp. 1611- 1614 ,(2006) , 10.1021/JA056112D
Yoshinori Yamamoto, From σ- to π-Electrophilic Lewis Acids. Application to Selective Organic Transformations Journal of Organic Chemistry. ,vol. 72, pp. 7817- 7831 ,(2007) , 10.1021/JO070579K
Barry M. Trost, New rules of selectivity: allylic alkylations catalyzed by palladium Accounts of Chemical Research. ,vol. 12, pp. 385- 393 ,(1980) , 10.1021/AR50155A001
El Mehdi Keramane, Bernard Boyer, Jean-Pierre Roque, Reactivity of bismuth(III) halides towards alcohols. A tentative to mechanistic investigation Tetrahedron. ,vol. 57, pp. 1909- 1916 ,(2001) , 10.1016/S0040-4020(01)00013-8
Barry M. Trost, David L. Van Vranken, Asymmetric Transition Metal-Catalyzed Allylic Alkylations. Chemical Reviews. ,vol. 96, pp. 395- 422 ,(1996) , 10.1021/CR9409804
Isao Shimizu, Kuok Meng Khien, Miki Nagatomo, Takayuki Nakajima, Akio Yamamoto, MOLYBDENUM-CATALYZED AROMATIC SUBSTITUTION WITH OLEFINS AND ALCOHOLS Chemistry Letters. ,vol. 1997, pp. 851- 852 ,(1997) , 10.1246/CL.1997.851
Friedrich Mühlthau, Daniel Stadler, Alain Goeppert, George A. Olah, G. K. Surya Prakash, Thorsten Bach, Chiral α-Branched Benzylic Carbocations: Diastereoselective Intermolecular Reactions with Arene Nucleophiles and NMR Spectroscopic Studies Journal of the American Chemical Society. ,vol. 128, pp. 9668- 9675 ,(2006) , 10.1021/JA062102G