Three-Component Annulation of Arynes with Phosphites and Ketones : Synthesis of Benzoxaphosphole 1-Oxides
- 주제(키워드) 유기화학
- 주제(DDC) 547
- 발행기관 아주대학교
- 지도교수 최준원
- 발행년도 2023
- 학위수여년월 2023. 2
- 학위명 석사
- 학과 및 전공 일반대학원 분자과학기술학과
- 실제URI http://www.dcollection.net/handler/ajou/000000032783
- 본문언어 영어
- 저작권 아주대학교 논문은 저작권에 의해 보호받습니다.
초록/요약
A mild and transition-metal-free three-component annulation was performed to obtain benzoxaphosphole 1-oxides using in situ formed arynes. We employed readily available substrates, 2-(trimethylsilyl)aryl triflates, phosphites, and ketones, as the three components; substrates with various functional groups, including the non-activated ketones, could be tolerated. The mechanistic study revealed that the pentavalent phosphorus intermediate might be produced through a three-component annulation and then converted to benzoxaphosphole 1-oxides, the desired compound, by hydrolysis in an aqueous workup step. Furthermore, we investigated the potential applications of this reaction by derivatizing the produced benzoxaphosphole 1-oxides. Our results improved the approaches to preparing organophosphorus compounds used in pharmaceuticals, materials, and natural products.
more목차
1. Introduction 1
2. Result and Discussion 3
2.1. Reaction Optimization 3
2.2. Substrates Scope 5
2.3. Mechanistic Study 11
2.4. Application 13
3.Conclusion 15
4. Experimental Procedure 16
4.1. General Information 16
4.2. Synthetic Procedure 17
5. Reference 73
