Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride

Xu，Yangsen1; Zhang，Zhaofei1; Qiu，Chuntian1; Chen，Shaoqin2; Ling，Xiang1; Su，Chenliang1

2020

10.1002/cssc.202002459

ChemSusChem   影响因子和分区

1864-5631

1864-564X

Photocatalytic water splitting technology (PWST) enables the direct use of water as appealing “liquid hydrogen source” for transfer hydrogenation reactions. Currently, the development of PWST-based transfer hydrogenations is still in an embryonic stage. Previous reports generally centered on the rational utilization of the in situ generated H-source (electrons) for hydrogenations, in which photogenerated holes were quenched by sacrificial reagents. Herein, the fully-utilization of the liquid H-source and holes during water splitting is presented for photo-reductive N-alkylation of nitro-aromatic compounds. In this integrate system, H-species in situ generated from water splitting were designed for nitroarenes reduction to produce amines, while alkanols were oxidized by holes for cascade alkylating of anilines as well as the generated secondary amines. More than 50 examples achieved with a broad range scope validate the universal applicability of this mild and sustainable coupling approach. The synthetic utility of this protocol was further demonstrated by the synthesis of existing pharmaceuticals via selective N-alkylation of amines. This strategy based on the sustainable water splitting technology highlights a significant and promising route for selective synthesis of valuable N-alkylated fine chemicals and pharmaceuticals from nitroarenes and amines with water and alkanols.

alkanol oxidation carbon nitride N-alkylation reaction photocatalysis water splitting

SCI ; EI

英语

其他

National Natural Science Foundation of China[21972094][21902105][21401190] ; China Postdoctoral Science Foundation[2019M653004] ; Shenzhen Innovation Program[JCYJ20170818142642395][JCYJ20190808142001745] ; Foundation for Distinguished Young Talents in Higher Education of Guangdong[2018KQNCX221]

Chemistry ; Science & Technology - Other Topics

Chemistry, Multidisciplinary ; Green & Sustainable Science & Technology

WOS:000592466600001

WILEY-V C H VERLAG GMBH

20204909596259

Aniline ; Alkylation ; Carbon nitride ; Water conservation ; Hydrogenation ; Liquefied gases

Water Resources:444 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

2-s2.0-85097164895

Scopus

1.SZU-NUS Collaborative Center and International Collaborative Laboratory of 2D,Materials for Optoelectronic Science & Technology of Ministry of Education,College of Optoelectronic Engineering,Shenzhen University,Shenzhen,518060,China
2.Department of Materials Science and Engineering,Southern University of Science and Technology,Shenzhen,518055,China

Xu，Yangsen,Zhang，Zhaofei,Qiu，Chuntian,et al. Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride[J]. ChemSusChem,2020,14(2):582-589.

Xu，Yangsen,Zhang，Zhaofei,Qiu，Chuntian,Chen，Shaoqin,Ling，Xiang,&Su，Chenliang.(2020).Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride.ChemSusChem,14(2),582-589.

Xu，Yangsen,et al."Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride".ChemSusChem 14.2(2020):582-589.