Bio-inspired iron-catalyzed oxidation of alkylarenes enables late-stage oxidation of complex methylarenes to arylaldehydes
Hu, PH (Hu, Penghui)[ 1,2 ] ; Tan, MX (Tan, Mingxi)[ 1,2 ] ; Cheng, L (Cheng, Lu)[ 1,2 ] ; Zhao, HY (Zhao, Hongyuan)[ 1,2 ] ; Feng, R (Feng, Rui)[ 2 ] ; Gu, WJ (Gu, Wei-Jin)[ 2 ] ; Han, W (Han, Wei)[ 1,2 ]*(韓維)
[ 1 ] Nanjing Normal Univ, Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Jiangsu Key Lab Biofunct Mat, Key Lab Appl Photochem, Wenyuan Rd 1, Nanjing 210023, Jiangsu, Peoples R China
[ 2 ] Nanjing Normal Univ, Sch Chem & Mat Sci, Wenyuan Rd 1, Nanjing 210023, Jiangsu, Peoples R China
NATURE COMMUNICATIONS,201906, 10
It is a long-standing challenge to achieve efficient and highly selective aerobic oxidation of methylarenes to benzaldehydes, owing to overoxidation problem stemming from the oxidizability of benzaldehyde far higher than the toluene under usual aerobic conditions. Herein we report a bio-inspired iron-catalyzed polymethylhydrosiloxane-promoted aerobic oxidation of methylarenes to benzaldehydes with high yields and selectivities. Notably, this method can tolerate oxidation-labile and reactive boronic acid group, which is normally required to be transformed immediately after its introduction, and represents a significant advance in the area of the chemistry of organoboronic acids, including the ability to incorporate both aldehyde and ketone functionalities into unprotected arylboronic acids, a class that can be difficult to access by current means. The robustness of this protocol is demonstrated on the late-stage oxidation of complex bioactive molecules, including dehydroabietic acid, Gemfibrozil, Tocopherol nicotinate, a complex polyol structure, and structurally complex arylboronic acids.
文章鏈接:
https://www.nature.com/articles/s41467-019-10414-7
版權(quán)與免責(zé)聲明:本網(wǎng)頁的內(nèi)容由收集互聯(lián)網(wǎng)上公開發(fā)布的信息整理獲得。目的在于傳遞信息及分享,并不意味著贊同其觀點或證實其真實性,也不構(gòu)成其他建議。僅提供交流平臺,不為其版權(quán)負責(zé)。如涉及侵權(quán),請聯(lián)系我們及時修改或刪除。郵箱:sales@allpeptide.com