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| Type |
Poster Presentation |
| Area |
Organic Chemistry |
| Room No. |
Event Hall |
| Time |
4월 19일 (목요일) 11:00~12:30 |
| Code |
ORGN.P-426 |
| Subject |
Synthesis of Dihaloketones through decarboxylative coupling reaction of Alkynoic Acids
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| Authors |
Eunjeong Cho, Myungjin Kim*, SeHyeon Han1,*, Sunwoo Lee*
Department of Chemistry, Chonnam National University, Korea
1Chonnam National University, Korea
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| Abstract |
Dichloroketone can be transformed for the synthesis of biologically active heterocyclic compounds and good building block candidate. Classical methods using chlorinating reagents such as Cl2, sulfuryl chloride, ammonium salt of tetrachloridoiodate, SiCl4/PhIO and CuCl2 required high temperature or harsh condition. Trichloroisocyanuric acid (TCCA) is known as chlorination reagent, inexpensive and stable.
As a much more efficient and convenient method, we developed the synthesis of dichloroketone by using the sequential reactions of coupling and chlorination. Arylbromide and propiolic acid were allowed to react in the presence of 5 mol% Pd(PPh3)2Cl2, 10 mol% dppb and 2.0 equivalent of DBU. The mixture was allowed to react with TCCA in CH3CN-H2O. The reactions with diarylalkyne and TCCA afforded the desired α,α-dichloroketones in moderate to good yields. In addition, they all were obtained from the sequential reaction of decarboxylative coupling and chlorination. This chlorination was conducted at room temperature and showed good tolerance toward functional groups such as chloride, bromide, aldehyde and ketone.
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| E-mail |
dms8096@gmail.com |
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121st General Meeting of the KCS