A one-pot and two-stage Baeyer-Villiger reaction using 2,2′-diperoxyphenic acid under biomolecule-compatible conditions†

Gan，Shaoyan1,5; Yin，Jingru1; Yu，Zhiyou1; Song，Lijuan1,2; Shi，Lei1,3,4,5

2022-02-11

10.1039/d1gc04478h

GREEN CHEMISTRY   影响因子和分区

1463-9262

1463-9270

An efficient oxidant named 2,2′-diperoxyphenic acid was newly developed, and it exhibited high stability as revealed by thermogravimetric analysis (TGA) coupled with differential scanning calorimetry (DSC). On applying this reagent in the Baeyer-Villiger oxidation, the reaction featured a markedly broad substrate scope and good functional group tolerance, giving rise to the corresponding products in good to excellent yields. Particularly, in the case of pure water or 1× Phosphate Buffered Saline (1× PBS) serving as the solvent, the protocol could work well, resulting in yields ranging from 81% to 98%. Moreover, the catalytic asymmetric version of the BV reaction was explored as well, affording the corresponding products in good yields and medium ee. Remarkably, the corresponding biological compatibility and greenness assessment indicated that this reagent had favorable application prospects in the biomedical and green manufacturing fields. Meanwhile, mechanistic studies including O isotope effect experiments and DFT computations suggested that this reaction followed the generally accepted mechanism of BV oxidation.

SCI ; EI

英语

通讯

WOS:000758982200001

20221311870159

Chemical reactions ; Saline water ; Thermogravimetric analysis

Water Resources:444 ; Chemistry:801 ; Chemical Reactions:802.2 ; Temperature Measurements:944.6

CHEMISTRY

2-s2.0-85127204431

Scopus

1.School of Science,Harbin Institute of Technology,Shenzhen,518055,China
2.Shenzhen Bay Laboratory,Shenzhen,518055,China
3.Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
4.State Key Laboratory of Elemento-Organic Chemistry,Nankai University,Tianjin,300071,China
5.School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin,150001,China

Gan，Shaoyan,Yin，Jingru,Yu，Zhiyou,等. A one-pot and two-stage Baeyer-Villiger reaction using 2,2′-diperoxyphenic acid under biomolecule-compatible conditions†[J]. GREEN CHEMISTRY,2022,24(5):2232-2239.

Gan，Shaoyan,Yin，Jingru,Yu，Zhiyou,Song，Lijuan,&Shi，Lei.(2022).A one-pot and two-stage Baeyer-Villiger reaction using 2,2′-diperoxyphenic acid under biomolecule-compatible conditions†.GREEN CHEMISTRY,24(5),2232-2239.

Gan，Shaoyan,et al."A one-pot and two-stage Baeyer-Villiger reaction using 2,2′-diperoxyphenic acid under biomolecule-compatible conditions†".GREEN CHEMISTRY 24.5(2022):2232-2239.