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Synfacts 2015; 11(1): 0081
DOI: 10.1055/s-0034-1379654
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Aryl Sulfamate and Tosylate Cross-Coupling with Aryl Grignard Reagents

Contributor(s):
Paul Knochel
,
Thomas Klatt
Agrawal T, Cook SP * Indiana University, Bloomington, USA
Iron-Catalyzed Coupling of Aryl Sulfamates and Aryl/Vinyl Tosylates with Aryl Grignards.

Org. Lett. 2014;
16: 5080-5083
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

iron - cross-coupling - Grignard reagents

Significance

The authors report the first iron-catalyzed direct coupling of aryl sulfamates and tosylates with aryl Grignard reagents. Interestingly, fluoride counterions were found to increase the yields of the desired products. FeF3 does not need to be reduced before the reaction, and in fact, reactions performed without the pre-reduction proceed better in almost all cases.


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Comment

The reaction was shown to tolerate a number of iron pre-catalysts with no significant homocoupling of the aryl Grignard. Studies to understand the reaction mechanism better are underway.


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