Unknown

Dataset Information

0

Visible-Light-Mediated Alkenylation, Allylation, and Cyanation of Potassium Alkyltrifluoroborates with Organic Photoredox Catalysts.


ABSTRACT: Iridium- and ruthenium-free approaches to protected allylic amines and alkyl nitriles under photoredox conditions are reported. An inexpensive organic dye, eosin Y, catalyzes coupling of Boc-protected potassium ?-aminomethyltrifluoroborates with a variety of substituted alkenyl sulfones through an ?-aminomethyl radical addition-elimination pathway. Allylic and homoallylic amines were formed in moderate yields with high E/Z selectivity. The mechanistic approach was extended using tosyl cyanide as a radical trap, enabling the conversion of alkyltrifluoroborates to nitriles via a Fukuzumi acridinium-catalyzed process.

SUBMITTER: Heitz DR 

PROVIDER: S-EPMC4994715 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

altmetric image

Publications

Visible-Light-Mediated Alkenylation, Allylation, and Cyanation of Potassium Alkyltrifluoroborates with Organic Photoredox Catalysts.

Heitz Drew R DR   Rizwan Komal K   Molander Gary A GA  

The Journal of organic chemistry 20160623 16


Iridium- and ruthenium-free approaches to protected allylic amines and alkyl nitriles under photoredox conditions are reported. An inexpensive organic dye, eosin Y, catalyzes coupling of Boc-protected potassium α-aminomethyltrifluoroborates with a variety of substituted alkenyl sulfones through an α-aminomethyl radical addition-elimination pathway. Allylic and homoallylic amines were formed in moderate yields with high E/Z selectivity. The mechanistic approach was extended using tosyl cyanide as  ...[more]

Similar Datasets

| S-EPMC5941304 | biostudies-literature
| S-EPMC6640734 | biostudies-literature
| S-EPMC5541851 | biostudies-literature
| S-EPMC5290490 | biostudies-literature
| S-EPMC4168922 | biostudies-literature
| S-EPMC7086342 | biostudies-literature
| S-EPMC4684717 | biostudies-literature
| S-EPMC8009506 | biostudies-literature
| S-EPMC4676763 | biostudies-literature
| S-EPMC6644467 | biostudies-literature