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학술발표회초록보기

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  • 03월 10일 13시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제105회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Searching for New Reactivity of Transition Metal Catalysts for the Efficient and Selective Organic Transformations

등록일
2010년 4월 6일 16시 01분 49초
접수번호
1495
발표코드
목2J1기념 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
목 11시 : 40분
발표형식
기념강연
발표분야
기념강연
저자 및
공동저자
장석복
KAIST 화학과, Korea
It has been discovered that a highly efficient, mild, and practical multi-component reaction for the synthesis of amidines, amdies, and imidates, which are prominent structural motifs in numerous bio-active natural products, important pharmacophores, synthetic intermediates, and efficient coordinating ligands. The electron deficient character of the sulfonyl substituent induces that the triazolyl intermediate makes progress toward the ketenimine by electron rearrangement and releasing dinitrogen. A new strategy for the synthesis of condensed hetero- and carbocycles such as pyrroloindoles or fluorenes has been developed that involve Pd-catalyzed cyclization of readily available N-(2-halobenzyl)pyrroles and their phenyl derivatives. The reaction is proposed to proceed via successive oxidative addition of benzylic halides to Pd(0) followed by base-assisted aromatic C-H bond activation. Thus, a broad range of condensed cyclic products were obtained in good to excellent yields. Silver-mediated intermolecular amination reactions of benzoxazoles were developed using formamides or parent amines as an amino group source. While the reaction with formamides requires rather harsh conditions, that with parent amines proceeds under milder conditions to afford 2-aminobenzoxazoles in high yields. Optically active amino groups could also be installed without racemization and significance of the present direct amination was demonstrated in one step synthesis of a biologically active coumarinyl benzoxazole derivative. References 1) Park, E. J.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2008, 130, 17268. 2) Hwang, S. J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2008, 130, 16158. 3) Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254. 4) Lee, J. M.; Park, E. J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2008, 130, 7824. 5) Cho, S. H.; Chang, S. Angew. Chem., Int. Ed. 2008, 47, 2836. 6) Cho, S. H.; Hwang, S. J.; Chang, S. Organic Syntheses 2008, 85, 131. 6) Kim, M.; Kwak, J.; Chang, S. Angew. Chem. Int. Ed. 2009, 48, 8935. 7) Cho, S. H.; Kim, J.; Lee, S. Y.; Chang, S. Angew. Chem. Int. Ed. 2009, 48, 9127.

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