Synthesis of Carboxylic Acids, Esters, and Amides from 1,1-Dibromoalkenes via Oxidation of Alkynyl Boronate Intermediates

被引:3
作者
Tao, Lei [1 ]
Yang, Wen [1 ]
Zhao, Wanxiang [1 ]
机构
[1] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Adv Catalyt Engn Res Ctr, Minist Educ,Coll Chem & Chem Engn, South Lushan Rd, Changsha 410082, Peoples R China
来源
CHEMISTRYSELECT | 2021年 / 6卷 / 33期
基金
中国国家自然科学基金;
关键词
Alkynyl boronates; Carboxylic acids; C(sp)-B bond oxidation; Corey-Fuchs reaction; 1; 1-Dibromoalkenes; C-H ACTIVATION; STEREOSELECTIVE-SYNTHESIS; PHOTOREDOX CATALYSIS; EFFICIENT SYNTHESIS; SECONDARY ALCOHOLS; COUPLING REACTIONS; ARYLBORONIC ACIDS; HYDROXYLATION; MILD; TRANSFORMATIONS;
D O I
10.1002/slct.202102150
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and practical method for the synthesis of carboxylic acids, esters, and amides from 1,1-dibromoalkenes has been developed. The reactions proceed through a key process, the C(sp)-B bond oxidation of alkynyl boronate intermediates with Oxone. This protocol features broad substrate scope, good efficiency, and good functional group compatibility. Moreover, the synthetic practicability was demonstrated by easy gram-scale preparation and the synthesis of drug molecules.
引用
收藏
页码:8532 / 8536
页数:5
相关论文
共 74 条
[1]   Synthesis of new N-aryl oxindoles as intermediates for pharmacologically active compounds [J].
Acemoglu, M ;
Allmendinger, T ;
Calienni, J ;
Cercus, J ;
Loiseleur, O ;
Sedelmeier, GH ;
Xu, D .
TETRAHEDRON, 2004, 60 (50) :11571-11586
[2]  
[Anonymous], 2018, ANGEW CHEM-GER EDIT, V130, P9928
[3]  
[Anonymous], 2008, Angew. Chem, V120, P3144
[4]  
[Anonymous], 2015, ANGEW CHEM-GER EDIT, V127, P1096
[5]  
[Anonymous], 2014, ANGEW CHEM-GER EDIT, V126, P6426
[6]  
[Anonymous], 2011, ANGEW CHEM, V123, P2821
[7]  
[Anonymous], 2018, ANGEW CHEM, V130, P7026
[8]  
[Anonymous], 2020, ANGEW CHEM, V132, P11005
[9]  
[Anonymous], 2010, ANGEW CHEM-GER EDIT, V122, P5268
[10]  
[Anonymous], 2012, Angew. Chem, V124, P808