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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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AgBF4-Induced Site-Selective Synthesis of 4-Sulfonylindoles in Au-Catalyzed Cyclization-Sulfonyl Migration Reactions
Itaru Nakamura1,2, Chunbo Jia2, Masahiro Terada2
1Institute For Excellence in Higher Education, Tohoku University, Sendai, Japan.
Abstract:
The reactions of ortho-alkynyl-N-arenesulfonylanilines in the presence of SPhosAuCl (2 mol %) and AgBF4 (6 mol %) produced the corresponding 4-sulfonylindoles in good yields with satisfactory site-selectivity at the C4-position of the indole ring. This reaction proceeded via cyclization followed by sequential [1,2]-rearrangement of the sulfonyl group. The selective migration of the sulfonyl group to the C4-position was induced by using an excess amount of AgBF4 relative to the gold catalyst to form a dinuclear Au─Ag complex to decelerate the migration to C3-position. Furthermore, the tetrafluoroborate anion with its suitable gold affinity and hydrogen bonding characteristics, plays a crucial role in enabling selective migration to the C4-position.
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