Prev. Article Next Article Table of Contents

Letter

Synthesis of Functionalized Diarylmethanes via a Copper-Catalyzed Cross-Coupling of Arylmagnesium Reagents with Benzylic Phosphates

Supporting Info

Christiane C. Kofink and Paul Knochel*

Department Chemie und Biochemie, Ludwig-Maximilians-Universitt, Butenandtstrasse 5-13, 81377 Mnchen, Germany

Org. Lett., 2006, 8 (18), pp 4121–4124

DOI: 10.1021/ol0616790

Publication Date (Web): August 3, 2006

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

, paul.knochel@cup.uni-muenchen.de

Abstract

A combination of copper chloride, triethyl phosphite, and tetrabutylammonium iodide is a very efficient catalytic system for the synthesis of polyfunctionalized diarylmethanes, using the cross-coupling reaction of arylmagnesium halides with benzylic phosphates. The antibiotic Trimethoprim has been prepared using this Cu(I)-catalyzed cross-coupling in 52% overall yield (four steps).

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue August 31, 2006
Received July 8, 2006

Recommend & Share

Related Content

Suzuki−Miyaura Cross-Coupling of Benzylic Phosphates with Arylboronic AcidsOrganic Letters
- Suzuki−Miyaura Cross-Coupling of Benzylic Phosphates with Arylboronic Acids
  Mark McLaughlin
  Organic Letters 2005 7 (22), pp 4875–4878
  Abstract: Suzuki−Miyaura cross-coupling of benzylic phosphates with arylboronic acids was investigated. Optimum conditions employed the simple catalytic system of palladium(II) acetate (1 mol %) and triphenylphosphine (4 mol %) with either potassium phosphate or ...
  Abstract | Full Text HTML | Hi-Res PDF
Cobalt(II)-Catalyzed Cross-Coupling between Polyfunctional Arylcopper Reagents and Aryl Fluorides or TosylatesOrganic Letters
- Cobalt(II)-Catalyzed Cross-Coupling between Polyfunctional Arylcopper Reagents and Aryl Fluorides or Tosylates
  Tobias J. Korn, Matthias A. Schade, Stefan Wirth, and Paul Knochel
  Organic Letters 2006 8 (4), pp 725–728
  Abstract: Organocopper compounds prepared by the transmetalation of functionalized arylmagnesium halides with CuCN·2LiCl undergo smooth cross-coupling reactions with aryl fluorides and tosylates bearing a carbonyl function in the ortho position in the presence of ...
  Abstract | Full Text HTML | Hi-Res PDF
Synthesis of Functionalized Nitroarylmagnesium Halides via an Iodine−Magnesium ExchangeThe Journal of Organic Chemistry
- Synthesis of Functionalized Nitroarylmagnesium Halides via an Iodine−Magnesium Exchange
  Ioannis Sapountzis, Henry Dube, Robert Lewis, Nina Gommermann, and Paul Knochel
  The Journal of Organic Chemistry 2005 70 (7), pp 2445–2454
  Abstract: Various nitro-substituted aryl and heteroaryl iodides undergo an iodine−magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures ...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Synthesis of Functionalized Diarylmethanes via a Copper-Catalyzed Cross-Coupling of Arylmagnesium Reagents with Benzylic Phosphates

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Suzuki−Miyaura Cross-Coupling of Benzylic Phosphates with Arylboronic Acids

Cobalt(II)-Catalyzed Cross-Coupling between Polyfunctional Arylcopper Reagents and Aryl Fluorides or Tosylates

Synthesis of Functionalized Nitroarylmagnesium Halides via an Iodine−Magnesium Exchange

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES