Gold‐ and Brønsted Acid‐Catalysed Deacyloxylative Cycloaromatisation of 1,6‐Diyne Esters to 11H‐Benzofluorenes and 13H‐Indenophenanthrenes
A synthetic method to prepare 11H‐benzo[a]fluorenes and 13H‐indeno[1,2‐l]phenanthrenes that relies on the gold(I)‐ and Brønsted acid‐mediated deacyloxylative cycloaromatisation of 1,6‐diyne esters under reaction conditions that did not require the exclusion of moisture or air is described. The react...
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Published in | Advanced synthesis & catalysis Vol. 364; no. 7; pp. 1313 - 1318 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
Heidelberg
Wiley Subscription Services, Inc
01.03.2022
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Subjects | |
Online Access | Get full text |
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Summary: | A synthetic method to prepare 11H‐benzo[a]fluorenes and 13H‐indeno[1,2‐l]phenanthrenes that relies on the gold(I)‐ and Brønsted acid‐mediated deacyloxylative cycloaromatisation of 1,6‐diyne esters under reaction conditions that did not require the exclusion of moisture or air is described. The reaction mechanism was delineated to involve an initial gold(I)‐catalysed 1,2‐acyloxy migration and 5‐exo‐trig cyclisation pathway. This was followed by 1,5‐enyne rearrangement and Brønsted acid‐assisted deacyloxylative aromatisation to give the polyaromatic hydrocarbon (PAH) product. |
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ISSN: | 1615-4150 1615-4169 |
DOI: | 10.1002/adsc.202200016 |