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Multifunctional Building Blocks Compatible with Photoredox-Mediated Alkylation for DNA-Encoded Library Synthesis.

Authors :
Badir SO
Sim J
Billings K
Csakai A
Zhang X
Dong W
Molander GA
Source :
Organic letters [Org Lett] 2020 Feb 07; Vol. 22 (3), pp. 1046-1051. Date of Electronic Publication: 2020 Jan 15.
Publication Year :
2020

Abstract

DNA-encoded library (DEL) technology has emerged as a novel interrogation modality for ligand discovery in the pharmaceutical industry. Given the increasing demand for a higher proportion of C(sp <superscript>3</superscript> )-hybridized centers in DEL platforms, a photoredox-mediated cross-coupling and defluorinative alkylation process is introduced using commercially available alkyl bromides and structurally diverse α-silylamines. Notably, no protecting group strategies for amines are necessary for the incorporation of a variety of amino-acid-based organosilanes, providing crucial branching points for further derivatization.

Details

Language :
English
ISSN :
1523-7052
Volume :
22
Issue :
3
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
31940210
Full Text :
https://doi.org/10.1021/acs.orglett.9b04568