Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C-N/C-S Bond Formation in Allylic Surrogates

doi:10.1002/chem.201805295

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	Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C-N/C-S Bond Formation in Allylic Surrogates
	Deng, Lei 2,3,4; Kleij, Arjan W.1,6; Yang, Weibo2,3,5
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2018-12-20
卷号	24 期号:72 页码:19156-19161
关键词	allylic substitution decarboxylation N-sulfonylhydrazones Pd catalysis vinylethylene carbonates
ISSN号	0947-6539
DOI	10.1002/chem.201805295
文献子类	Article
英文摘要	Switchable catalytic transformation of reactants can be a powerful approach towards diversity-orientated synthesis from easily available molecular synthons. Herein, an endogenous ligand-controlled, Pd-catalyzed allylic substitution allowing for either selective C-N or C-S bond formation using vinylethylene carbonates (VECs) and N-sulfonylhydrazones as coupling partners has been developed. This versatile methodology provides a facile, divergent route for the highly chemo- and stereoselective synthesis of functional allylic sulfones or sulfonohydrazides. The newly developed protocol features wide substrate scope (nearly 80 examples), broad functional group tolerance, and potential for the late-stage functionalization of bioactive compounds. The isolation and crystallographic analysis of a catalytically competent pi-allyl Pd complex suggests that the pathway leading to the allylic products proceeds through a different manifold as previously proposed for the functionalization of VECs with nucleophiles.
资助项目	Chinese NSF[21702217] ; 100 talent program of Chinese Academy of Sciences[00000000] ; 1000-Youth Talents Plan, Shanghai-Youth Talent, Shanghai-Technology innovation Action Plan[18JC1415300] ; CERCA Program/Generalitat de Catalunya[00000000] ; ICREA[00000000] ; Spanish MINECO[CTQ2017-88920-P] ; AGAUR[2017-SGR-232]
WOS关键词	VINYLETHYLENE CARBONATES ; N-TOSYLHYDRAZONES ; ENANTIOSELECTIVE CONSTRUCTION ; CYCLOADDITION ; SUBSTITUTION ; HETEROCYCLES ; FENOFIBRATE ; ACCESS ; WATER
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000453829200008
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/279464]
专题	分子影像中心（筹）
通讯作者	Kleij, Arjan W.; Yang, Weibo
作者单位	1.Inst Chem Res Catalonia ICIQ, Ave Paisos Catalans 16, Tarragona 43007, Spain; 2.Chinese Acad Sci, Key Lab Receptor Res, Shanghai Inst Mat Med, Shanghai, Peoples R China; 3.Univ Chinese Acad Sci, Beijing, Peoples R China; 4.Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Jiangsu, Peoples R China; 5.Univ Sci & Technol Liaoning, Anshan 114051, Peoples R China; 6.Catalan Inst Res & Adv Studies ICREA, Pg Lluis Co 23, Barcelona 08010, Spain
推荐引用方式 GB/T 7714	Deng, Lei,Kleij, Arjan W.,Yang, Weibo. Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C-N/C-S Bond Formation in Allylic Surrogates[J]. CHEMISTRY-A EUROPEAN JOURNAL,2018,24(72):19156-19161.
APA	Deng, Lei,Kleij, Arjan W.,&Yang, Weibo.(2018).Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C-N/C-S Bond Formation in Allylic Surrogates.CHEMISTRY-A EUROPEAN JOURNAL,24(72),19156-19161.
MLA	Deng, Lei,et al."Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C-N/C-S Bond Formation in Allylic Surrogates".CHEMISTRY-A EUROPEAN JOURNAL 24.72(2018):19156-19161.