Unknown

Dataset Information

0

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


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 ?-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.

SUBMITTER: Kubiak RW 

PROVIDER: S-EPMC5521008 | BioStudies | 2016-01-01

REPOSITORIES: biostudies

Similar Datasets

2018-01-01 | S-EPMC7232104 | BioStudies
2015-01-01 | S-EPMC5426858 | BioStudies
2018-01-01 | S-EPMC6035867 | BioStudies
2018-01-01 | S-EPMC6650386 | BioStudies
2016-01-01 | S-EPMC4900183 | BioStudies
2014-01-01 | S-EPMC4608551 | BioStudies
1000-01-01 | S-EPMC4648053 | BioStudies
1000-01-01 | S-EPMC4832834 | BioStudies
1000-01-01 | S-EPMC5810544 | BioStudies
2017-01-01 | S-EPMC5521013 | BioStudies