Noncryogenic I/Br−Mg Exchange of Aromatic Halides Bearing Sensitive Functional Groups Using i-PrMgCl−Bis[2-(N,N-dimethylamino)ethyl] Ether Complexes

Xiao-jun Wang,* Xiufeng Sun, Li Zhang, Yibo Xu, Dhileepkumar Krishnamurthy, and Chris H. Senanayake
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877
Org. Lett., 2006, 8 (2), pp 305–307
DOI: 10.1021/ol052704p
Publication Date (Web): December 23, 2005
Copyright © 2006 American Chemical Society
*

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

, xwang@rdg.boehringer-ingelheim.com

Abstract

Abstract Image

Iodo- and bromoaromatics bearing sensitive carboxylic ester and cyano groups underwent a selective halide−magnesium exchange with isopropylmagnesium chloride at ambient temperature in the presence of bis[2-(N,N-dimethylamino)ethyl] ether to afford the corresponding Grignard reagents. The newly formed reactive Grignard reagents were allowed to react with electrophiles such as trimethylborate to afford arylboronic acids in good to excellent yields.

Tools

History

  • Published In Issue January 19, 2006
  • Received November 8, 2005

Recommend & Share

Related Content

Other ACS content by these authors: