Photoinduced Alcohol and Ketone Generation from Alkoxyaroylsilanes: Mechanistic Insights into Competing Radical Pathways.

Yang Cheng, Shu-Lin Zhang, Jessika Lammert, Le Yu, Yinjiao Zhao, Armido Studer, Jiani Ma, Yu Fang

Abstract read

In one paragraph

Article in JACS Au, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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0citing papers in PubMed

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1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

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3 · Its place in the literature

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0 citing papers in PubMed.

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4 · The record

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5 · Who and what money

Authors and funding

8 authors.

Yang ChengKey Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, Shaanxi Provincial Key Laboratory of New Concept Sensors and Molecular Materials, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Shu-Lin ZhangKey Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, Shaanxi Provincial Key Laboratory of New Concept Sensors and Molecular Materials, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Jessika LammertInstitute of Organic Chemistry, University of Münster, Corrensstrasse 40, 48149 Münster, Germany.

Le YuKey Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710127, China.ORCID https://orcid.org/0000-0002-0360-290X

Yinjiao ZhaoKey Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, Shaanxi Provincial Key Laboratory of New Concept Sensors and Molecular Materials, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Armido StuderInstitute of Organic Chemistry, University of Münster, Corrensstrasse 40, 48149 Münster, Germany.ORCID https://orcid.org/0000-0002-1706-513X

Jiani MaKey Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, Shaanxi Provincial Key Laboratory of New Concept Sensors and Molecular Materials, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.ORCID https://orcid.org/0000-0003-3325-0762

Yu FangKey Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, Shaanxi Provincial Key Laboratory of New Concept Sensors and Molecular Materials, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.ORCID https://orcid.org/0000-0001-8490-8080

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Acylsilanes represent a unique class of organosilicon compounds with distinctive photochemical reactivities, including hydrogen atom transfer (HAT) and silyl shift pathways. Recently, a new photolabile protecting group (PPG) benzoyldiisopropylsilane (BDIPS) featuring an acylsilane functionality was introduced for alcohol protection. While the photomediated deprotection of aliphatic silyl ethers in methanol provided the free alcohols, BDIPS-protected benzyl or allyl alcohols resulted in rearranged ketones upon photoexcitation in acetonitrile. In this work, we systematically investigate the photochemical behavior of different BDIPS-ethers, focusing on the mechanistic divergence leading to either alcohol release as PPG or rearranging ketone formation. Through a combined approach of femtosecond transient absorption spectroscopy and density functional theory calculations, we elucidate the competing reaction pathways for model compounds

Indexed as

acylsilanephotochemistryphotolabile protecting grouptheoretical calculationsultrafast spectroscopy

Identifiers

PMID41450625

DOI10.1021/jacsau.5c01342

PMCPMC12728622

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.