Hypervalent Iodine Promoted the Synthesis of Cycloheptatrienes and Cyclopropanes

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Feb 7

PMID 35126980

Authors

Da-Fu Yuan

Zi-Chen Wang

Rui-Sen Geng

Guang-Yi Ren

James S Wright

Shao-Fei Ni

Ming Li

Li-Rong Wen

Lin-Bao Zhang

Affiliations

Soon will be listed here.

Abstract

A new strategy is reported for intramolecular Buchner-type reactions using PIDA as a promotor. Traditionally, the Buchner reaction is achieved Rh-carbenoids derived from Rh catalysts with diazo compounds. Herein, the first metal-free Buchner-type reaction to construct highly strained cycloheptatriene- and cyclopropane-fused lactams is presented. The advantage of these transformations is in their mild reaction conditions, simple operation, broad functional group compatibility and rapid synthetic protocol. In addition, scaled-up experiments and a series of follow-up synthetic procedures were performed to clarify the flexibility and practicability of this method. DFT calculations were carried out to clarify the mechanism.

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