Catalytic Allylation of Aldehydes Using Unactivated Alkenes

Simple feedstock organic molecules, especially alkenes, are attractive starting materials in organic synthesis because of their wide availability. Direct utilization of such bulk, inert organic molecules for practical and selective chemical reactions, however, remains limited. Herein, we developed a...

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Published inJournal of the American Chemical Society Vol. 142; no. 28; pp. 12374 - 12381
Main Authors Tanabe, Shun, Mitsunuma, Harunobu, Kanai, Motomu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.07.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
NOZAKI-HIYAMA ALLYLATION
RADICAL-CATION
PHOTOREDOX
BIS(OXAZOLINE) LIGANDS
RATE CONSTANTS
CARBONYL-COMPOUNDS
PALLADIUM COMPLEX
C-H BONDS
ASYMMETRIC ALLYLATION
C(SP)-H FUNCTIONALIZATION
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Summary:Simple feedstock organic molecules, especially alkenes, are attractive starting materials in organic synthesis because of their wide availability. Direct utilization of such bulk, inert organic molecules for practical and selective chemical reactions, however, remains limited. Herein, we developed a ternary hybrid catalyst system comprising a photoredox catalyst, a hydrogen-atom-transfer catalyst, and a chromium complex catalyst, enabling catalytic allylation of aldehydes with simple alkenes, including feedstock lower alkenes. The reaction proceeded under visible-light irradiation at room temperature and with high functional group tolerance. The reaction was extended to an asymmetric variant by employing a chiral chromium complex catalyst.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c04735