Cp*Co(III)-Catalyzed C(8)-Nucleophilic Cascade Cyclization of Quinoline N-Oxide with 1,6-Enyne.Org Lett. 2023 Mar 31; 25(12):2018-2023.OL
Abstract
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.
Links
Pub Type(s)
Journal Article
Language
eng
PubMed ID
36926924
Citation
Garai, Bholanath, et al. "Cp*Co(III)-Catalyzed C(8)-Nucleophilic Cascade Cyclization of Quinoline N-Oxide With 1,6-Enyne." Organic Letters, vol. 25, no. 12, 2023, pp. 2018-2023.
Garai B, Ali MR, Mandal R, et al. Cp*Co(III)-Catalyzed C(8)-Nucleophilic Cascade Cyclization of Quinoline N-Oxide with 1,6-Enyne. Org Lett. 2023;25(12):2018-2023.
Garai, B., Ali, M. R., Mandal, R., & Sundararaju, B. (2023). Cp*Co(III)-Catalyzed C(8)-Nucleophilic Cascade Cyclization of Quinoline N-Oxide with 1,6-Enyne. Organic Letters, 25(12), 2018-2023. https://doi.org/10.1021/acs.orglett.3c00305
Garai B, et al. Cp*Co(III)-Catalyzed C(8)-Nucleophilic Cascade Cyclization of Quinoline N-Oxide With 1,6-Enyne. Org Lett. 2023 Mar 31;25(12):2018-2023. PubMed PMID: 36926924.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Cp*Co(III)-Catalyzed C(8)-Nucleophilic Cascade Cyclization of Quinoline N-Oxide with 1,6-Enyne.
AU - Garai,Bholanath,
AU - Ali,Molla Rahamat,
AU - Mandal,Rajib,
AU - Sundararaju,Basker,
Y1 - 2023/03/16/
PY - 2023/3/18/medline
PY - 2023/3/18/pubmed
PY - 2023/3/17/entrez
SP - 2018
EP - 2023
JF - Organic letters
JO - Org Lett
VL - 25
IS - 12
N2 - 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.
SN - 1523-7052
UR - https://www.unboundmedicine.com/medline/citation/36926924/Cp_Co_III__Catalyzed_C_8__Nucleophilic_Cascade_Cyclization_of_Quinoline_N_Oxide_with_16_Enyne_
DB - PRIME
DP - Unbound Medicine
ER -
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