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. 2016 Jul 1;18(13):3118-21.
doi: 10.1021/acs.orglett.6b01298. Epub 2016 Jun 22.

Enantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles

Robert W Kubiak 2nd  1 , Jeffrey D Mighion  1 , Sidney M Wilkerson-Hill  1 , Joshua S Alford  1 , Tetsushi Yoshidomi  2   3 , Huw M L Davies  1
Affiliations

Enantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles

Robert W Kubiak 2nd et al. Org Lett. .

Abstract

The enantioselective intermolecular sp(3) C-H functionalization at the allylic and benzylic positions was achieved using rhodium-catalyzed reactions with 4-phenyl-N-(methanesulfonyl)-1,2,3-triazole. The optimum dirhodium tetracarboxylate catalyst for these reactions was Rh2(S-NTTL)4. The rhodium-bound α-imino carbene intermediates preferentially reacted with tertiary over primary C-H bonds in good yields and moderate levels of enantioselectivity (66-82% ee). This work demonstrates that N-sulfonyltriazoles can be applied to the effective C-H functionalization at sp(3) C-H bonds of substrates containing additional functionality.

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Figures

Figure 1
Figure 1
Substrate scope for benzylic C–H functionalization reaction.
Scheme 1
Scheme 1
Previous work on intermolecular C–H functionalization using N-sulfonyl-1,2,3-triazoles.
Scheme 2
Scheme 2
Reaction of triazole 1 with 4-methylanisole
See this image and copyright information in PMC

References

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