Electron Donor-Acceptor Complex-Enabled Autoinductive Conversion of Acylnitromethanes to Acylnitrile Oxides in a Photochemical Machetti-De Sarlo Reaction: Synthesis of 5-Substituted 3-Acylisoxazoles

被引：1

作者：

Arunkirirote, Piyaporn ^{[1
]}

Suwalak, Pornteera ^{[1
]}

Chaisan, Nattawadee ^{[2
]}

Tummatorn, Jumreang ^{[1
,2
,3
]}

Ruchirawat, Somsak ^{[1
,2
,3
]}

Thongsornkleeb, Charnsak ^{[1
,2
,3
]}

机构：

[1] Chulabhorn Res Inst, Lab Med Chem, Bangkok 10210, Thailand

[2] Chulabhorn Grad Inst, Program Chem Sci, Bangkok 10210, Thailand

[3] Minist Higher Educ Sci Res & Innovat MHESI, Ctr Excellence Environm Hlth & Toxicol EHT, Off Permanent Secretary OPS, Bangkok 10400, Thailand

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 43期

关键词：

NITRO-COMPOUNDS; CONDENSATION; CATALYSIS; OXIDATION; ALDEHYDES; KETONES;

D O I：

10.1021/acs.orglett.4c02708

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photochemical Machetti-De Sarlo reaction has been developed for preparing 5-substituted 3-acylisoxazoles from acylnitromethanes and terminal alkynes. This photochemical protocol utilizes an innovative electron donor-acceptor complex, generated in situ from acylnitromethanes, catalytic (LiOBu)-Bu-t, and 1,1,1,3,3,3-hexafluoro-2-propanol, as a photosensitizer to promote rapid conversion with a broad substrate scope in up to 80% efficiency. A sigmoidal autoinductive kinetic profile is revealed, demonstrating the novel and unique dual catalysis in the first photochemical approach of this reaction.

引用

页码：9173 / 9178

页数：6