Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes

doi:10.1038/s41467-024-53728-x

	Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes
	Xu, Yuanli 1; Chen, Wenlong 2; Pu, Ruihua3 ; Ding, Jia 2; An, Qing 2; Yang, Yi 1; Liu, Weimin3 ; Zuo, Zhiwei 2
	2024-10-30
发表期刊	NATURE COMMUNICATIONS (IF:14.7[JCR-2023],16.1[5-Year])
EISSN	2041-1723
卷号	15 期号:1
发表状态	已发表
DOI	10.1038/s41467-024-53728-x
摘要	["The selective incorporation of a deuterium atom into small molecules with high selectivity is highly valuable for medical and chemical research. Unfortunately, this remains challenging due to the complete deuteration caused by commonly used hydrogen isotope exchange strategies. We report the development of a photocatalytic selective monodeuteration protocol utilizing C-C bond as the unconventional functional handle. The synergistic combination of radical-mediated C-C bond scission and deuterium atom transfer processes enables the effective constructions of benzylic CDH moieties with high selectivity for monodeuteration. The combinational use of a bisphosphonium photocatalyst, thiol catalyst, and CH3OD deuteration agent provides operationally simple conditions for photocatalytic monodeuteration. Moreover, the photoinduced electron transfer process of the bisphosphonium photocatalyst is elucidated through a series of spectroscopy experiments, identifying a peculiar back electron transfer process that can be regulated by subsequent nucleophilic additions.","Incorporation of deuterium into small molecules in the place of hydrogens can alter the properties of the molecule in ways that provide benefits without affecting the core function of the molecule. Here, the authors report a ring-opening deuteration of cyclic alkanes via biphosphonium photocatalysis."]
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收录类别	SCI
语种	英语
资助项目	National Natural Science Foundation of China (National Science Foundation of China)[2021YFA1500100] ; National Key R&D Program of China["22125111","21971163"] ; National Natural Science Foundation of China[21XD1424600] ; Natural Science Foundation of Shanghai[XDB0610000]
WOS研究方向	Science & Technology - Other Topics
WOS类目	Multidisciplinary Sciences
WOS记录号	WOS:001346144300001
出版者	NATURE PORTFOLIO
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/483950
专题	物质科学与技术学院物质科学与技术学院_PI研究组_刘伟民组
通讯作者	Yang, Yi; Liu, Weimin; Zuo, Zhiwei
作者单位	1.Sichuan Univ Sci & Engn, Sichuan Inst Higher Educ, Innovat Ctr Chenguang High Performance Fluorine Ma, Key Lab Green Chem, Zigong 643000, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China 3.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
通讯作者单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Xu, Yuanli,Chen, Wenlong,Pu, Ruihua,et al. Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes[J]. NATURE COMMUNICATIONS,2024,15(1).
APA	Xu, Yuanli.,Chen, Wenlong.,Pu, Ruihua.,Ding, Jia.,An, Qing.,...&Zuo, Zhiwei.(2024).Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes.NATURE COMMUNICATIONS,15(1).
MLA	Xu, Yuanli,et al."Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes".NATURE COMMUNICATIONS 15.1(2024).