有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
総説および総合論文
トリアゾールをカルベン錯体の前駆体として用いる触媒反応の開発
三浦 智也
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ジャーナル 認証あり

73 巻 (2015) 12 号 p. 1200-1211

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N-Sulfonyl-1,2,3-triazoles are readily prepared by a copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of terminal alkynes with sulfonyl azides. Their ring-chain tautomerization generates α-imino diazo compounds, although the equilibrium lies far to the triazole form in general. Transition metal catalysts, especially rhodium(II) carboxylate dimers, can efficiently trap the transient α-imino diazo compounds to give α-imino metal carbene complexes with the extrusion of molecular nitrogen. These metal carbene complexes share many features with the well-known α-oxo metal carbene complexes derived from α-dizao carbonyl compounds. However, in some cases, the presence of the nucleophilic imino nitrogen endows their unique reactivity depending on the reactants as well as the catalysts. In this article, we describe nickel(0) and rhodium(II)-catalyzed inter- and intramolecular reactions of N-sulfonyl-1,2,3-triazoles with various types of reactants such as carbon, oxygen, and sulfur nucleophiles, which provide a facile method for the synthesis of nitrogen-containing compounds. These reactions are successfully applied to all-in one-pot reactions starting from terminal alkynes.

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