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 inAdvanced synthesis & catalysis Vol. 364; no. 7; pp. 1313 - 1318
Main Authors Baratay, Corentin Antoine, Li, Wenhai, Mathiew, Mitch, Yu, Lei, Kyne, Sara Helen, Rao, Weidong, Hong Chan, Philip Wai
Format Journal Article
LanguageEnglish
Published Heidelberg Wiley Subscription Services, Inc 01.03.2022
Subjects
Esters
Gold
Moisture effects
Polycyclic aromatic hydrocarbons
Reaction mechanisms
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Abstract 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.
AbstractList 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.
Author Kyne, Sara Helen
Li, Wenhai
Rao, Weidong
Baratay, Corentin Antoine
Hong Chan, Philip Wai
Yu, Lei
Mathiew, Mitch
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SubjectTerms Esters
Gold
Moisture effects
Polycyclic aromatic hydrocarbons
Reaction mechanisms
Title Gold‐ and Brønsted Acid‐Catalysed Deacyloxylative Cycloaromatisation of 1,6‐Diyne Esters to 11H‐Benzofluorenes and 13H‐Indenophenanthrenes
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