The dearomatization of heterocycles has been a powerful means for producing functional molecules in synthesis. In the case of pyrroles, reductive methods (such as the Birch reduction) have been most widely exploited, while oxidative methods are generally dismissed as too difficult or unpredictable to be useful. However, since the early twentieth century considerable research has been carried out on the controlled oxidation of pyrroles to give highly functionalized products, using a variety of oxidants. This review presents a summary of all work up until the present day in the area of pyrrole oxidation, looking at the use of peroxide, singlet oxygen, hypervalent iodine reagents, a range or organic and inorganic oxidants, and electrochemical approaches. It also offers some perspective on the potential future role of pyrrole oxidation in synthesis.

Item Type:	Refereed Article
Keywords:	heterocycles
Research Division:	Chemical Sciences
Research Group:	Organic Chemistry
Research Field:	Organic Chemical Synthesis
Objective Division:	Expanding Knowledge
Objective Group:	Expanding Knowledge
Objective Field:	Expanding Knowledge in the Chemical Sciences
UTAS Author:	Howard, JK (Mr James Howard)
UTAS Author:	Rihak, KJ (Mr Kieran Rihak)
UTAS Author:	Bissember, AC (Dr Alex Bissember)
UTAS Author:	Smith, JA (Associate Professor Jason Smith)
ID Code:	109316
Year Published:	2016
Web of Science® Times Cited:	22
Deposited By:	Chemistry
Deposited On:	2016-06-08
Last Modified:	2017-11-10
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