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  • 02월 28일 19시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제111회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Palladium(II) Catalyzed ortho-Arylation via Phosphate Group Directed C-H Activation

등록일
2013년 2월 21일 16시 18분 55초
접수번호
1427
발표코드
ORGN.O-8 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
금 11시 : 45분
발표형식
구두발표
발표분야
유기화학 - Oral Presentation for Young Organic Chemists
저자 및
공동저자
전우형, 문봉진, 강재효*
서강대학교 화학과, Korea
Transition metal-catalysed C-H activation is an attractive approach in aryl-aryl coupling reactions because it bypasses the use of a pre-activated aryl group such as aryl halide or aryl triflates. However, a directing group is typically required to dictate the regioselectivity of the coupling reactions. Good coordinating groups such as aldehyde, ketone, imine, ester, amide, and triazene are known to be efficient in assisting the ortho-C-H bond activation with high regioselectivity. In the case of phenol, temporal transformation of the phenol group into a good directing group and removal of the temporal group after the coupling reaction strategy has been generally used. Some of the examples for the temporal directing group include phenol ester, phenoxypyrimidine, phenol carbamates, and phenylphosphinite. The common feature of these directing groups is that they are highly polarizable and exhibit strong coordinating ability. While one of the convenient and efficient transformation methods for phenol masking is phosphorylation, the utility of phosphate group as an ortho-directing group in C-H activated aryl-aryl coupling reaction has not been reported so far, probably due to its poor coordinating abilities. In this presentation, we wish to report the first successful example of palladium catalysed ortho-arylation via phosphate group-directed C?H activation. Aryl dialkyl phosphate, which is readily available from phenol, turned out to be not only a good substrate for Pd(II) catalyzed aryl-aryl coupling reaction through ortho-C-H activation but also a good precursor for the consecutive C-C bond formation via reductive cleavage and the subsequent alkylation of the resulting aryl anion.

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