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Catalytic Azido‐Hydrazination of Alkenes Enabled by Visible Light: Mechanistic Studies and Synthetic Applications
Author(s) -
Wang Peng,
Luo Yunxuan,
Zhu Songsong,
Lu Dengfu,
Gong Yuefa
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901041
Subject(s) - chemistry , photoredox catalysis , azide , reagent , catalysis , combinatorial chemistry , fluorenone , visible spectrum , alkyl , photochemistry , moiety , radical , organic chemistry , photocatalysis , polymer , physics , optoelectronics , fluorene
A visible‐light‐enabled catalytic intermolecular azido‐hydrazination method for unactivated alkenes is developed via an orderly radical addition sequence. This transformation features metal‐free and redox‐neutral conditions and is applicable to a wide range of alkenes with commercially available reagents. Mechanistic and kinetic studies reveal that the efficient generation of azide radical enabled by fluorenone under visible‐light is critical to this methodology. The β ‐azido alkyl hydrazines prepared with this reaction can be conveniently derived to valuable synthetic building blocks, and one of the products has been successfully applied in the total synthesis of (±)‐ibrutinib, which is used to treat B cell cancers.