Radicals masquerading as electrophiles: Dual orbital effects in nitrogen-philic acyl radical cyclization and related addition reactions

Carl H. Schiesser, Uta Wille, Hiroshi Matsubara, Ilhyong Ryu

研究成果: Article同行評審

114 引文 斯高帕斯(Scopus)

摘要

Free-radical chemistry has come a long way in a relatively short period of time. The synthetic practitioner takes for granted the wealth of mechanistic and rate constant data now available and can apply free-radical techniques to the synthesis of many different classes of target molecule with confidence. Despite this, there are still mechanistic anomalies that need to be addressed. This Account highlights recent work involving nucleophilic radicals with low-lying unoccupied orbitais, such as acyl, oxyacyl, silyl, stannyl, and germyl radicals. Through interesting singly occupied molecular orbital (SOMO)-π* and highest occupied molecular orbital (HO-MO)-lowest unoccupied molecular orbital (LUMO) interactions during these reactions, the radicals involved are able to mask as electrophiles, providing high levels of regiocontrol and efficient methods for the synthesis of important heterocycles.

原文English
頁(從 - 到)303-313
頁數11
期刊Accounts of Chemical Research
40
發行號5
DOIs
出版狀態Published - 1 五月 2007

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