ortho-Bromo(propa-1,2-dien-1-yl)arenes : substrates for domino reactions

Masters, Kye-Simeon, Wallesch, Manuela, & Bräse, Stefan (2011) ortho-Bromo(propa-1,2-dien-1-yl)arenes : substrates for domino reactions. The Journal of Organic Chemistry, 76(21), pp. 9060-9067.

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Abstract

o-Bromo(propa-1,2-dien-1-yl)arenes exhibit novel and orthogonal reactivity under Pd catalysis in the presence of secondary amines to form enamines (concerted Pd insertion, intramolecular carbopalladation, and terminative Buchwald–Hartwig coupling) and of amides to form indoles (addition, Buchwald–Hartwig cyclization, and loss of the acetyl group). The substrates for these reactions can be accessed in a reliable and highly selective two-step process from 2-bromoaryl bromides.

Impact and interest:

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ID Code: 69692
Item Type: Journal Article
Refereed: Yes
DOI: 10.1021/jo201679s
ISSN: 0022-3263
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > ORGANIC CHEMISTRY (030500) > Organic Chemical Synthesis (030503)
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2011 American Chemical Society
Copyright Statement: This article is freely available from the American Chemical Society website 12 months after the publication date. See links to publisher website in this record
Deposited On: 02 Apr 2014 23:02
Last Modified: 15 May 2014 06:26

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