An extensive review on transition metal catalyzed indole C H activation: Catalyst selection and mechanistic insights DOI Creative Commons
Colette M. St. Mary,

D. Vasudevan,

P. Nagarajan

et al.

Polyhedron, Journal Year: 2024, Volume and Issue: unknown, P. 117260 - 117260

Published: Oct. 1, 2024

Language: Английский

Rhodium-Catalyzed Atroposelective C–H Alkylation of 1-Aryl Isoquinoline Derivatives with Cyclopropanols DOI
Wenwen Zhang, Quannan Wang, Chao Zheng

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4017 - 4024

Published: Feb. 20, 2025

Language: Английский

Citations

3
Metal‐Free Arylation of Benzothiophenes at C4 by Activation as their Benzothiophene S‐Oxides DOI Creative Commons

Ranjana Bisht,

Mihai V. Popescu, Zhen He

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(29)

Published: March 31, 2023

Abstract Benzothiophenes, activated by oxidation to the corresponding S ‐oxides, undergo C−H/C−H‐type coupling with phenols give C4 arylation products. While an electron‐withdrawing group at C3 of benzothiophene is important, process operates without a directing and metal catalyst, thus rendering it compatible sensitive functionalities—e.g. halides formyl groups. Quantum chemical calculations suggest formal stepwise mechanism involving heterolytic cleavage aryloxysulfur species π‐complex phenoxonium cation. Subsequent addition cation position favored over C3; Fukui functions predict that major regioisomer formed more electron‐rich between C4. Varied selective manipulation products showcase synthetic utility metal‐free process.

Language: Английский

Citations

14
Strained cycloalkanols in C–C bond formation reactions: a boon in disguise! DOI
Neha Jha, P. Mishra, Manmohan Kapur

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4941 - 4971

Published: Jan. 1, 2023

A summary of the various ring opening reactions strained and unstrained cycloalkanols is elaborated in present review. Key emphasis on reactivities pertaining to cyclopropanols, cyclobutanols higher analogues provided.

Language: Английский

Citations

14
Arylation of Cyclopropanol with Pyrrole: Asymmetric Synthesis of Indolizidine 167B, Indolizidine 209D, and Monomorine I DOI

Shuangwei Liu,

Xiaojiao Su,

Dan Jiang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(12), P. 2058 - 2062

Published: March 17, 2023

A Fe(NO3)3-mediated ring-opening arylation of cyclopropanol with the electron-rich pyrrole has been developed, which might proceed through oxidative radical ring opening followed by cyclization to motif and then aromatization. This method enables direct without prefunctionalization thus allows rapid access a diverse array chiral 5,6,7,8-tetrahydroindolizines from easily available amino acid esters. The synthetic utility demonstrated asymmetric synthesis alklaoids (-)-indolizidine 167B, (+)-indolizidine 209D, (+)-monomorine I, natural product analogue.

Language: Английский

Citations

11
Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles DOI
Roger Machín Rivera,

Zack R. Ferrin,

Vincent N. G. Lindsay

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4738 - 4743

Published: May 29, 2024

A concise synthetic approach to medicinally relevant pyrroloindolones and related fused heterocycles is reported via the diastereoselective

Language: Английский

Citations

4
Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols DOI

Xueying Yang,

Yuanshuang Xu, Xinying Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 694 - 694

Published: Jan. 1, 2025

Language: Английский

Citations

0
Synthesis of 3‐Hydroxyfluorenones Based on the Cascade Reaction of Aryl Enaminones with Benzyl Substituted Cyclopropanols DOI

Xueying Yang,

Yuanshuang Xu,

Shasha Ye

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: June 4, 2025

Comprehensive Summary Presented herein is a novel synthesis of 3‐hydroxyfluorenones through the cascade reaction aryl enaminones with benzyl substituted cyclopropanols. The formation product initiated by introduction an enone moiety onto enaminone cyclopropanol as homoenolate precursor C−H bond activation, followed intramolecular enamine Michael addition, enol amine elimination and aromatization‐driven oxidative dehydrogenation. To our knowledge, this should be first example for specific 3‐hydroxyfluorenone derivatives via simultaneous both indenone phenol scaffolds C−H/C−C/C−N activation three C−C formation. In general, newly developed protocol features easily accessible substrates, synthetically pharmaceutically valuable products, unique pathway, good compatibility various functional groups ready scalability.

Language: Английский

Citations

0
Site-Selective C8-Alkylation of Quinolines with Cyclopropanols: Merging C–H/C–C Bond Activation DOI
Santu Mandal, Tripti Paul, Pallab Karjee

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7805 - 7809

Published: Oct. 23, 2023

The site-selective C8-alkylation of quinolines has been accomplished using cyclopropyl alcohols as the alkylating agents and N-oxide a weak chelating group in presence Co(III) catalysis via merging C-H/C-C bond activation. use cyclopropanol alkyl source, Co catalysis, substrate scope, HRMS analysis reaction intermediate, late-stage mutation drug molecules/natural products are important practical features.

Language: Английский

Citations

8
Transition-Metal-Catalyzed Directed C8–H Carbon–Carbon Bond Formation in Quinolines and 1,2,3,4-Tetrahydroquinolines DOI
Tharmalingam Punniyamurthy, Shubhajit Basak, Tripti Paul

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(21), P. 3454 - 3469

Published: March 20, 2023

Abstract C8-Substituted quinoline (QN) and 1,2,3,4-tetrahydroquinoline (THQ) scaffolds are featured in numerous bioactive compounds natural products. Appreciable efforts have been made towards the development of elegant techniques to functionalize C8–H bond QNs THQs. The transition-metal-catalyzed chelation-assisted C–H activation strategy has emerged as an effective synthetic tool among existing methods. This review focuses on recent advances directed carbon–carbon forming reactions for functionalization THQs (till February 2023). discussion categorized based type reaction. 1 Introduction 2 Acylation 3 Alkylation 4 Alkenylation 5 Alkynylation 6 Allylation 7 Annulation 8 Arylation 9 Conclusion Outlook

Language: Английский

Citations

7
Zinc‐Mediated Diastereoselective Annulation of Cyclopropanols with Alkylidenemalononitriles via Enolized Homoenolate DOI

Kento Tsukiji,

Takeru Hayakawa,

Kazuya Kanemoto

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 13, 2023

Abstract A zinc‐mediated annulation reaction between cyclopropanols and alkylidenemalononitriles is reported. The promoted in the presence of Et 2 Zn 1,4‐diazabicyclo[2.2.2]octane (DABCO) DMSO at 80 °C, affording cyclopropane‐fused 6‐amino‐3,4‐dihydro‐2 H ‐pyran‐5‐carbonitrile derivatives moderate to good yields with high diastereoselectivity. proposed involve an enolized homoenolate as key reactive intermediate, which generated through ring opening zinc cyclopropoxide enolization resulting homoenolate. enolate moiety this species undergoes Michael addition alkylidenemalononitrile, followed by closure α‐functionalized intramolecular cyclization one cyano groups.

Language: Английский

Citations

7