Sunlight-Driven Decarboxylative Alkynylation of α-Keto Acids with Bromoacetylenes by Hypervalent Iodine Reagent Catalysis: A Facile Approach to Ynones

Hui Tan; Hongji Li; Wangqin Ji; Lei Wang

doi:10.1002/anie.201503479

Sunlight-Driven Decarboxylative Alkynylation of α-Keto Acids with Bromoacetylenes by Hypervalent Iodine Reagent Catalysis: A Facile Approach to Ynones

Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8374-7. doi: 10.1002/anie.201503479. Epub 2015 Jun 1.

Authors

Hui Tan¹, Hongji Li¹, Wangqin Ji¹, Lei Wang^{2

3}

Affiliations

¹ Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000 (PR China).
² Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000 (PR China). leiwang@chnu.edu.cn.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (PR China). leiwang@chnu.edu.cn.

PMID: 26031476
DOI: 10.1002/anie.201503479

Abstract

A novel and practical decarboxylative alkynylation of α-keto acids with bromoacetylenes is catalyzed by hypervalent iodine(III) reagents when irradiation by sunlight at room temperature. The product ynones are generated in good yields. Experiments show that results obtained with blue light (λ=450-455 nm) are comparable to those obtained when using sunlight. Mechanistic studies demonstrate that the sunlight-driven decarboxylation undergoes a radical process.

Keywords: acylation; alkynes; hypervalent compounds; photochemistry; radicals.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylene / chemistry*
Acylation
Alkynes / chemistry*
Catalysis
Decarboxylation
Halogenation
Iodine / chemistry*
Keto Acids / chemistry*
Ketones / chemical synthesis*
Ketones / chemistry
Sunlight

Substances

Alkynes
Keto Acids
Ketones
Iodine
Acetylene