Sequential N-arylation of primary amines as a route to alkyldiarylamines

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 6019-6022

  Harris, Michele C ^a   Geis, Oliver ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL ARYL ETHER; DIAMINE;

ARTICLE; CONFORMATIONAL TRANSITION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033529898     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990568u     Document Type: Article

References (20)

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16. (rac)-PPF-OMe = 1-[2-(Diphenylphosphino)ferrocenyl]ethyl methyl ether: (a) Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138. (b) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
17. (rac)-PPF-OMe = 1-[2-(Diphenylphosphino)ferrocenyl]ethyl methyl ether: (a) Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138. (b) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
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20. Note: The first aryl bromide has also been used as the limiting reagent. The procedure is identical to that given, except that the stoichiometry for the first arylation is 1.4:1.2:1.0 (base:amine:aryl halide). In the second arylation, the aryl bromide is used in 20% excess. The modified procedures are denoted as A′, B′, C′ or D′.