PDF icon Download PDF
Synfacts 2012; 8(2): 0193
DOI: 10.1055/s-0031-1290007
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Fe-Catalyzed Cross-Coupling of Alkyl Halides with Alkynyl Grignard Reagents

Contributor(s):
Paul Knochel
,
Andreas K. Steib
Hatakeyama T, Okada Y, Yoshimoto Y, Nakamura M * Kyoto University, Japan
Tuning Chemoselectivity in Iron-Catalyzed Sonogashira-Type Reactions Using a Bisphosphine Ligand with Peripheral Steric Bulk: Selective Alkynylation of Nonactivated Alkyl Halides.

Angew. Chem. Int. Ed. 2011;
50: 10973-10976
CrossrefSearch in Google Scholar
Further Information

Publication History

Publication Date:
19 January 2012 (online)

 
 PDF Download Permissions and Reprints

Key words

iron - alkynes - cross-coupling

Significance

The authors report a novel coupling of primary and secondary alkyl halides with alkynylmagnesium reagents with iron catalysis. The use of a bisphosphine ligand bearing peripheral steric bulk as well as slow addition of the Grignard reagent suppress undesired side reactions.


 

Comment

By using starting materials with two potential reactive sites, for example C(sp3)–Br and C(sp2)–OTf, and applying the reported iron-catalyzed cross-coupling with an alkynyl Grignard reagent, the C(sp)–C(sp3)-coupled products are obtained in excellent yields.


 

 


  Permissions and Reprints