Chemodivergent Couplings of N-Arylureas and Methyleneoxetanones via Rh(III)-Catalyzed and Solvent-Controlled C-H Activation

被引:27
作者
Zhu, Guoxun [1 ]
Shi, Wendi [1 ,2 ,3 ,4 ]
Gao, Hui [2 ,3 ,4 ]
Zhou, Zhi [2 ,3 ,4 ]
Song, Huacan [1 ]
Yi, Wei [2 ,3 ,4 ]
机构
[1] Sun Yat Sen Univ, Sch Chem Engn & Technol, Guangzhou 510275, Guangdong, Peoples R China
[2] Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China
[3] Guangzhou Med Univ, Sch Pharmaceut Sci, State Key Lab Resp Dis, Guangzhou 511436, Guangdong, Peoples R China
[4] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China
关键词
METHYLENE-BETA-LACTONES; TRANSITION-METAL; ROOM-TEMPERATURE; BOND ACTIVATION; STEREOSELECTIVE-SYNTHESIS; DIRECTING GROUPS; ARYL UREAS; FUNCTIONALIZATION; ALLYLATION; PHENOXYACETAMIDES;
D O I
10.1021/acs.orglett.9b01333
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient couplings of diverse N-arylureas and methyleneoxetanones have been realized via Rh(III)-catalyzed and solvent-controlled chemoselective C-H functionalization, which involved the tunable beta-H elimination and beta-O elimination processes, thereby giving divergent access to quinolin-2(1H)-ones and ortho-allylated N-arylureas with broad substrate compatibility and good functional group tolerance. the divergent synthetic utilities of the transformations have also been exemplified by subsequently tandem C-H allylation, unsymmetrical C-H functionalization, alternative reaction mode, as well as removal of the carbamoyl group.
引用
收藏
页码:4143 / 4147
页数:5
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