Prev. Article Next Article Table of Contents

Article

One-Pot Synthetic Routes to Multiply Substituted Indene Derivatives by Hydrolysis of Zirconocene-Mediated Intermolecular Coupling Reactions of Aromatic Ketones and Alkynes

Supporting Info

Zhenfeng Xi,*^† Ruiyun Guo,^† Shizue Mito,^‡ Hongliang Yan,^† Ken-ichiro Kanno,^‡ Kiyohiko Nakajima,^§ and Tamotsu Takahashi*^‡

Peking UniversityHokkaido University Joint Lab, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China, Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University, and CREST, Japan Science and Technology Corporation (JST), Sapporo 060-0811, Japan, and Department of Chemistry, Aichi University of Education, Igaya, Kariya 448-8542, Japan

J. Org. Chem., 2003, 68 (4), pp 1252–1257

DOI: 10.1021/jo025828d

Publication Date (Web): January 14, 2003

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

Peking University.

‡

Hokkaido University.

Aichi University of Education.

, tamotsu@cat.hokudai.ac.jp

Abstract

Two one-pot multicomponent synthetic methods for highly substituted indenes are described. The intermolecular coupling of aromatic ketones with alkynes on low-valent zirconocene species generates oxazirconacyclopentenes, which upon hydrolysis with 20% HCl for 3 h afforded indene derivatives in good to excellent yields. Similarly, the pair-selective coupling of two identical or different alkynes bearing at least one aromatic substituent formed zirconacyclopentadienes. Quenching of the reaction mixture with concentrated H₂SO₄ also results in the formation of highly substituted indenes in high yields.

View: Full Text HTML | Hi-Res PDF