Journal
ORGANIC LETTERS
Volume 25, Issue 12, Pages 2018-2023Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c003052018
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This study demonstrates the C(8)-selective nucleophilic cascade cyclization of quinoline N-oxide with easily derived 1,6-enyne from phenol derivatives. Various quinoline N-oxide and alkynes are found to be suitable for producing a library of quinoline N-oxide tethered cis-hydrobenzofurans with high yields and excellent functional group tolerance. The utility of the protocol has been achieved through post-synthetic modification of the cyclized product. Mechanistic studies reveal a base-assisted internal electrophilic-type substitution (BIES)-type pathway for C-H bond activation, and electrospray ionization mass spectrometry (ESI-MS) analysis confirms the formation of a key five-membered cobaltacycle.
The C(8)-selective nucleophilic cascade cyclization of quinoline N-oxide with easily derived 1,6-enyne from phenol derivatives is demonstrated. A variety of quinoline N-oxide and alkynes are discovered to be suitable for producing a library of quinoline N-oxide tethered cis-hydrobenzofurans with high yields and excellent functional group tolerance. The utility of the protocol has been accomplished by post-synthetic modification of the cyclized product. The mechanistic studies indicate a base-assisted internal electrophilic-type substitution (BIES)-type pathway for C-H bond activation, and electrospray ionization mass spectrometry (ESI-MS) analysis of the stoichiometric reaction confirmed the formation of a key five-membered cobaltacycle.
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