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. 2012 Jul 20;14(14):3796-9.
doi: 10.1021/ol301681z. Epub 2012 Jul 3.

Iron-catalyzed alkylations of aryl sulfamates and carbamates

Amanda L Silberstein  1 , Stephen D Ramgren, Neil K Garg
Affiliations

Iron-catalyzed alkylations of aryl sulfamates and carbamates

Amanda L Silberstein et al. Org Lett. .

Abstract

The alkylation of aryl sulfamates and carbamates using iron catalysis is reported. The method constructs sp(2)-sp(3) carbon-carbon bonds and provides synthetically useful yields across a range of substrates (>35 examples). The directing group ability of sulfamates and carbamates, accompanied by their low reactivity toward conventional cross-couplings, renders these substrates useful for the synthesis of polyfunctionalized arenes.

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Figures

Figure 1
Figure 1
Iron-catalyzed alkylation of aryl sulfamates and carbamates.
Figure 2
Figure 2
Optimal result obtained after extensive optimization.
Figure 3
Figure 3
Sequential site-selective couplings and assembly of 7.
See this image and copyright information in PMC

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