☆ 4.5 Article

Cationic organoaluminum compounds as intramolecular hydroamination catalysts

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2012)

期刊

JOURNAL OF ORGANOMETALLIC CHEMISTRY

卷 696, 期 26, 页码 4179-4183

出版社

ELSEVIER SCIENCE SA

DOI: 10.1016/j.jorganchem.2011.09.010

关键词

Hydroamination; Cationic; Alkyl aluminum; Aryl aluminum; Catalysis; Cyclization

类别

Chemistry, Inorganic & Nuclear Chemistry, Organic

资金

National Science Foundation [CHE 0718446, CHE 03422510]

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摘要

Cationic dialkylaluminum and m-terphenylalkylaluminum compounds catalyze the intramolecular hydroamination of primary and secondary aminopentenes. The reaction rates are strongly dependent on the substrate and the catalyst substituents. The bulky species [Dipp*AlEt][CHB11H5I6] (Dipp* = 2,6-Dipp(2)C(6)H(3)-, Dipp = 2,6-iPr(2)C(6)H(3)-), 4, was the most active catalyst. Although the neutral species DcpAlEt(2) (Dcp = 2,6-(2,6-Cl2C6H3)(2)C6H3-), 7, and Dipp*AlEt2, 8, showed some catalytic activity, they were more than 25 times less reactive than their cationic counterparts [DcpAlEt][CHB11H5Cl6], 3, and 4. The cyclization of secondary benzylaminopentenes with [Et2Al][CHB11H5I6], 1, was strongly dependent on the substitution of the C-2 olefinic carbon. (C) 2011 Elsevier B.V. All rights reserved.

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