Prev. Article Next Article Table of Contents

Letter

Effective Monoallylation of Anilines Catalyzed by Supported KF

Supporting Info

Vittorio Pace, Fernando Martínez, María Fernández, Jose V. Sinisterra, and Andrés R. Alcántara*

Organic and Pharmaceutical Chemistry Department, Pharmacy Faculty, Complutense University, 28040-Madrid, Spain

Org. Lett., 2007, 9 (14), pp 2661–2664

DOI: 10.1021/ol070890o

Publication Date (Web): June 13, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, andresr@farm.ucm.es

Abstract

A mild and straightforward monoallylation procedure for different anilines is described using the efficient, inexpensive, noncorrosive, and environmentally friendly reagent KF-Celite. By using only a 1/1.2 stoichiometric ratio of electrophilic reagent to aniline, in very short reaction times, the monoallylated products are obtained in high isolated yields via this procedure, which works very effectively regardless of the electronic nature of the substituent on the ring, although electron withdrawing groups make the reactions go even faster.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue July 05, 2007
Received April 17, 2007

Recommend & Share

Related Content

Direct Use of Allylic Alcohols for Platinum-Catalyzed Monoallylation of AminesOrganic Letters
- Direct Use of Allylic Alcohols for Platinum-Catalyzed Monoallylation of Amines
  Masaru Utsunomiya, Yoshiki Miyamoto, Junji Ipposhi, Takashi Ohshima, and Kazushi Mashima
  Organic Letters 2007 9 (17), pp 3371–3374
  Abstract: A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a π-allylplatinum intermediate without the use of an ...
  Abstract | Full Text HTML | Hi-Res PDF
Synthesis of Epoxides by Palladium-Catalyzed Reactions of Tertiary Allyl Alcohols with Aryl or Alkenyl HalidesJournal of the American Chemical Society
- Synthesis of Epoxides by Palladium-Catalyzed Reactions of Tertiary Allyl Alcohols with Aryl or Alkenyl Halides
  Sayuri Hayashi, Hideki Yorimitsu and Koichiro Oshima
  Journal of the American Chemical Society 2009 131 (6), pp 2052–2053
  Abstract: A novel synthetic method for the preparation of tri- or tetrasubstituted epoxides is reported. Treatment of readily available tertiary allyl alcohol with aryl or alkenyl halide under palladium catalysis resulted in arylative cyclization to form the ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
[(NHC)Au^I]-Catalyzed Acid-Free Alkyne Hydration at Part-per-Million Catalyst LoadingsJournal of the American Chemical Society
- [(NHC)Au^I]-Catalyzed Acid-Free Alkyne Hydration at Part-per-Million Catalyst Loadings
  Nicolas Marion, Rubn S. Ramn and Steven P. Nolan
  Journal of the American Chemical Society 2009 131 (2), pp 448–449
  Abstract: A highly efficient [(NHC)Au^I]-based (NHC = N-heterocyclic carbene) catalytic system for the hydration of an array of alkynes that operates under acid-free conditions and at very low catalyst loadings (typically 50−100 ppm and as low as 10 ppm) was ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Letter

Effective Monoallylation of Anilines Catalyzed by Supported KF