Suzuki–Miyaura coupling of aryl fluorosulfates in water: a modified approach for the synthesis of novel coumarin derivatives under mild conditions

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Suzuki–Miyaura coupling of aryl fluorosulfates in water: a modified approach for the synthesis of novel coumarin derivatives under mild conditions. / Joy, Muthipeedika; Sajith, Ayyiliath; Santra, Sougata et al.
In: Journal of Taibah University for Science, Vol. 18, No. 1, 2347679, 2024.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{3da5fc1ce8274d0bab7f9229cb133347,

title = "Suzuki–Miyaura coupling of aryl fluorosulfates in water: a modified approach for the synthesis of novel coumarin derivatives under mild conditions",

abstract = "We herein report a modified, eco-friendly and atom-economical approach for the synthesis of a series of novel coumarin analogues via Suzuki–Miyaura cross-coupling methodology under mild conditions. The utilization of coumarin fluorosulfate as an atom-economical pseudohalide based electrophilic coupling partner was the key for success of our modified methodology. In addition, the use of water as a solvent, exceptionally milder reaction conditions and traditional catalytic systems further demonstrates the synthetic utility of the developed protocol. A comparative study of different pseudohalide leaving groups has been carried out in the later stage to understand the efficiency of aryl fluorosulfate. From this study, the increased hydrophilic nature of the fluorosulfate electrophilic coupling partner when compared to the other electrophiles has been realized. This allowed the increased solubility of the fluorosulfate electrophile in water under milder temperature conditions thereby furnishing the desired products in good to excellent yields. {\textcopyright} 2024 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.",

author = "Muthipeedika Joy and Ayyiliath Sajith and Sougata Santra and Dhananjay Bhattacherjee and Nikolai Beliaev and Grigory Zyryanov and Oleg Eltsov and Karickal Haridas and Mohammed Alshammari",

note = "Grigory Zyryanov is thankful to Ministry of Science and Higher Education of the Russian Federation (Agreement # 075-15-2022-1118, dated 29 June 2022). Sougata Santra is thankful to Russian Science Foundation (Grant # 24-23-00516). This study is supported via funding from Prince Satam bin Abdulaziz University project number (PSAU/2023/R/1444).",

year = "2024",

doi = "10.1080/16583655.2024.2347679",

language = "English",

volume = "18",

journal = "Journal of Taibah University for Science",

issn = "1658-3655",

publisher = "Taibah University",

number = "1",

}

RIS

TY - JOUR

T1 - Suzuki–Miyaura coupling of aryl fluorosulfates in water: a modified approach for the synthesis of novel coumarin derivatives under mild conditions

AU - Joy, Muthipeedika

AU - Sajith, Ayyiliath

AU - Santra, Sougata

AU - Bhattacherjee, Dhananjay

AU - Beliaev, Nikolai

AU - Zyryanov, Grigory

AU - Eltsov, Oleg

AU - Haridas, Karickal

AU - Alshammari, Mohammed

N1 - Grigory Zyryanov is thankful to Ministry of Science and Higher Education of the Russian Federation (Agreement # 075-15-2022-1118, dated 29 June 2022). Sougata Santra is thankful to Russian Science Foundation (Grant # 24-23-00516). This study is supported via funding from Prince Satam bin Abdulaziz University project number (PSAU/2023/R/1444).

PY - 2024

Y1 - 2024

N2 - We herein report a modified, eco-friendly and atom-economical approach for the synthesis of a series of novel coumarin analogues via Suzuki–Miyaura cross-coupling methodology under mild conditions. The utilization of coumarin fluorosulfate as an atom-economical pseudohalide based electrophilic coupling partner was the key for success of our modified methodology. In addition, the use of water as a solvent, exceptionally milder reaction conditions and traditional catalytic systems further demonstrates the synthetic utility of the developed protocol. A comparative study of different pseudohalide leaving groups has been carried out in the later stage to understand the efficiency of aryl fluorosulfate. From this study, the increased hydrophilic nature of the fluorosulfate electrophilic coupling partner when compared to the other electrophiles has been realized. This allowed the increased solubility of the fluorosulfate electrophile in water under milder temperature conditions thereby furnishing the desired products in good to excellent yields. © 2024 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.

AB - We herein report a modified, eco-friendly and atom-economical approach for the synthesis of a series of novel coumarin analogues via Suzuki–Miyaura cross-coupling methodology under mild conditions. The utilization of coumarin fluorosulfate as an atom-economical pseudohalide based electrophilic coupling partner was the key for success of our modified methodology. In addition, the use of water as a solvent, exceptionally milder reaction conditions and traditional catalytic systems further demonstrates the synthetic utility of the developed protocol. A comparative study of different pseudohalide leaving groups has been carried out in the later stage to understand the efficiency of aryl fluorosulfate. From this study, the increased hydrophilic nature of the fluorosulfate electrophilic coupling partner when compared to the other electrophiles has been realized. This allowed the increased solubility of the fluorosulfate electrophile in water under milder temperature conditions thereby furnishing the desired products in good to excellent yields. © 2024 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85192136624

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001219486800001

U2 - 10.1080/16583655.2024.2347679

DO - 10.1080/16583655.2024.2347679

M3 - Article

VL - 18

JO - Journal of Taibah University for Science

JF - Journal of Taibah University for Science

SN - 1658-3655

IS - 1

M1 - 2347679

ER -

ID: 56648575