2022
DOI: 10.1002/anie.202213086
|View full text |Cite
|
Sign up to set email alerts
|

Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer

Abstract: The synthesis of 2‐azetidinones (β‐lactams) from simple acrylamide starting materials by visible‐light‐mediated energy transfer catalysis is reported. The reaction features a C(sp3)−H functionalization via a variation of the Norrish–Yang photocyclization involving a carbon‐to‐carbon 1,5‐hydrogen atom transfer (supported by deuterium labelling and DFT calculations) and can be used for the construction of a diverse range of β‐lactam products.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
5

Citation Types

0
11
0

Year Published

2023
2023
2024
2024

Publication Types

Select...
9

Relationship

0
9

Authors

Journals

citations
Cited by 31 publications
(11 citation statements)
references
References 89 publications
(11 reference statements)
0
11
0
Order By: Relevance
“…Visible-light-mediated energy transfer (EnT) catalysis has emerged as an efficient and valuable alternative, enabling access to reactive triplet states and facilitating subsequent organic transformations. Inspired by the remarkable progress in EnT catalysis, we reasoned that the EnT method may enable the activation of N -tosylhydrazone due to its inherent weak N–S bond strength. , With the release of sulfonyl groups and nitrogen, an in situ triplet-state carbene species should be formed and subsequently facilitate the generation of highly congested EWG-free cyclopropanes with 1,1-disubstituted alkenes. Considering this possibility, we undertook the challenge and designed an EnT-mediated σ-bond homolysis toward the activation of N -tosylhydrazones and the synthesis of highly congested cyclopropanes bearing contiguous all-carbon quaternary centers (Scheme D).…”
Section: Introductionmentioning
confidence: 99%
“…Visible-light-mediated energy transfer (EnT) catalysis has emerged as an efficient and valuable alternative, enabling access to reactive triplet states and facilitating subsequent organic transformations. Inspired by the remarkable progress in EnT catalysis, we reasoned that the EnT method may enable the activation of N -tosylhydrazone due to its inherent weak N–S bond strength. , With the release of sulfonyl groups and nitrogen, an in situ triplet-state carbene species should be formed and subsequently facilitate the generation of highly congested EWG-free cyclopropanes with 1,1-disubstituted alkenes. Considering this possibility, we undertook the challenge and designed an EnT-mediated σ-bond homolysis toward the activation of N -tosylhydrazones and the synthesis of highly congested cyclopropanes bearing contiguous all-carbon quaternary centers (Scheme D).…”
Section: Introductionmentioning
confidence: 99%
“…Considering that C sp 3 –C sp 3 bond formation is a part of almost all synthetic efforts, 10 a C sp 3 –Br bond is introduced as the first domino of the cyclization cascade (Scheme 1C). 11 However, direct alkylation involving alkyl bromide usually requires the catalysis of transition metals or photocatalysts (Ru, Ir, Acr + , etc .)…”
Section: Introductionmentioning
confidence: 99%
“…13 More recently, the Petersen group have further developed a visible-light-mediated convenient and straightforward procedure for the synthesis of β-lactams from simple and easy to obtain acrylamide precursors via intramolecular H-shift. 14 In continuation of our interest in visible-light photochemistry 15 and inspired by the remarkable advances in visible-light-mediated energy transfer (EnT) catalysis, we have directed our efforts toward the development of a visible light induced method for intramolecular hydroarylation. Reported herein is a novel and efficient protocol to access phenanthrene-9,9(10 H )-dicarbonitrile derivatives from 2-malononitrilemethylene-substituted 1,1′-biphenyls through visible light-induced cyclization involving [1,5] H-shift by using 2,4,5,6-tetrakis(carbazol-9-yl)-1,3-dicyanobenzene (4CzIPN) as a photocatalyst under mild conditions.…”
Section: Introductionmentioning
confidence: 99%