Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents

Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale throug...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2023-08, Vol.25 (33), p.6200-6205
Main Authors: Yedase, Girish Suresh, Arif, Munaifa, Kuniyil, Rositha, Yatham, Veera Reddy
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a345t-62e21193172798a5f8fa140968a1baebe257991f68f3533a46272bf48af6f24b3
cites cdi_FETCH-LOGICAL-a345t-62e21193172798a5f8fa140968a1baebe257991f68f3533a46272bf48af6f24b3
container_end_page 6205
container_issue 33
container_start_page 6200
container_title Organic letters
container_volume 25
creator Yedase, Girish Suresh
Arif, Munaifa
Kuniyil, Rositha
Yatham, Veera Reddy
description Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale through simply cyclocondensation of commercially available anthranilamide with phenyltrifluoro or difluoromethyl ketone. Preliminary mechanistic studies indicated that a canonical photoredox catalytic cycle is being operative. DFT studies support this and further reveal that deprotonation occurs before radical cleavage. DFT studies also show that the better yield with HCF2 reagent is attributed to the favorable expulsion of the corresponding radical moiety.
doi_str_mv 10.1021/acs.orglett.3c02413
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2850718241</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2850718241</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-62e21193172798a5f8fa140968a1baebe257991f68f3533a46272bf48af6f24b3</originalsourceid><addsrcrecordid>eNp9kE1Lw0AQhhdRbK3-AkFy9JJ2P5Ls5ljrR4WCovUcNulsk7rN1t0Nkn9vSmNP4mmG4X1mmAeha4LHBFMykYUbG7vW4P2YFZhGhJ2gIYkpCzmO6emxT_AAXTi3wZh0k_QcDRiPuRAkGaLNa2m8KaSXuvVVEczblTXB0laT-0rpxlizBV-2WvrK1IFRwVR_Qg0u-K58GdxBXZTBu5e5hr-heh28gVxD7d0lOlNSO7jq6wh9PD4sZ_Nw8fL0PJsuQsmi2IcJBUpIyginPBUyVkJJEuE0EZLkEnKgMU9TohKhWMyYjBLKaa4iIVWiaJSzEbo97N1Z89WA89m2cgVoLWswjcuoiDEnYu9rhNghWljjnAWV7Wy1lbbNCM72krNOctZLznrJHXXTH2jyLayOzK_VLjA5BPb0xjS27v79d-UPe5uMpQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2850718241</pqid></control><display><type>article</type><title>Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Yedase, Girish Suresh ; Arif, Munaifa ; Kuniyil, Rositha ; Yatham, Veera Reddy</creator><creatorcontrib>Yedase, Girish Suresh ; Arif, Munaifa ; Kuniyil, Rositha ; Yatham, Veera Reddy</creatorcontrib><description>Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale through simply cyclocondensation of commercially available anthranilamide with phenyltrifluoro or difluoromethyl ketone. Preliminary mechanistic studies indicated that a canonical photoredox catalytic cycle is being operative. DFT studies support this and further reveal that deprotonation occurs before radical cleavage. DFT studies also show that the better yield with HCF2 reagent is attributed to the favorable expulsion of the corresponding radical moiety.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.3c02413</identifier><identifier>PMID: 37578816</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2023-08, Vol.25 (33), p.6200-6205</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-62e21193172798a5f8fa140968a1baebe257991f68f3533a46272bf48af6f24b3</citedby><cites>FETCH-LOGICAL-a345t-62e21193172798a5f8fa140968a1baebe257991f68f3533a46272bf48af6f24b3</cites><orcidid>0000-0002-3967-5342</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37578816$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yedase, Girish Suresh</creatorcontrib><creatorcontrib>Arif, Munaifa</creatorcontrib><creatorcontrib>Kuniyil, Rositha</creatorcontrib><creatorcontrib>Yatham, Veera Reddy</creatorcontrib><title>Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale through simply cyclocondensation of commercially available anthranilamide with phenyltrifluoro or difluoromethyl ketone. Preliminary mechanistic studies indicated that a canonical photoredox catalytic cycle is being operative. DFT studies support this and further reveal that deprotonation occurs before radical cleavage. DFT studies also show that the better yield with HCF2 reagent is attributed to the favorable expulsion of the corresponding radical moiety.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kE1Lw0AQhhdRbK3-AkFy9JJ2P5Ls5ljrR4WCovUcNulsk7rN1t0Nkn9vSmNP4mmG4X1mmAeha4LHBFMykYUbG7vW4P2YFZhGhJ2gIYkpCzmO6emxT_AAXTi3wZh0k_QcDRiPuRAkGaLNa2m8KaSXuvVVEczblTXB0laT-0rpxlizBV-2WvrK1IFRwVR_Qg0u-K58GdxBXZTBu5e5hr-heh28gVxD7d0lOlNSO7jq6wh9PD4sZ_Nw8fL0PJsuQsmi2IcJBUpIyginPBUyVkJJEuE0EZLkEnKgMU9TohKhWMyYjBLKaa4iIVWiaJSzEbo97N1Z89WA89m2cgVoLWswjcuoiDEnYu9rhNghWljjnAWV7Wy1lbbNCM72krNOctZLznrJHXXTH2jyLayOzK_VLjA5BPb0xjS27v79d-UPe5uMpQ</recordid><startdate>20230825</startdate><enddate>20230825</enddate><creator>Yedase, Girish Suresh</creator><creator>Arif, Munaifa</creator><creator>Kuniyil, Rositha</creator><creator>Yatham, Veera Reddy</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3967-5342</orcidid></search><sort><creationdate>20230825</creationdate><title>Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents</title><author>Yedase, Girish Suresh ; Arif, Munaifa ; Kuniyil, Rositha ; Yatham, Veera Reddy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-62e21193172798a5f8fa140968a1baebe257991f68f3533a46272bf48af6f24b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yedase, Girish Suresh</creatorcontrib><creatorcontrib>Arif, Munaifa</creatorcontrib><creatorcontrib>Kuniyil, Rositha</creatorcontrib><creatorcontrib>Yatham, Veera Reddy</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yedase, Girish Suresh</au><au>Arif, Munaifa</au><au>Kuniyil, Rositha</au><au>Yatham, Veera Reddy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2023-08-25</date><risdate>2023</risdate><volume>25</volume><issue>33</issue><spage>6200</spage><epage>6205</epage><pages>6200-6205</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale through simply cyclocondensation of commercially available anthranilamide with phenyltrifluoro or difluoromethyl ketone. Preliminary mechanistic studies indicated that a canonical photoredox catalytic cycle is being operative. DFT studies support this and further reveal that deprotonation occurs before radical cleavage. DFT studies also show that the better yield with HCF2 reagent is attributed to the favorable expulsion of the corresponding radical moiety.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>37578816</pmid><doi>10.1021/acs.orglett.3c02413</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3967-5342</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2023-08, Vol.25 (33), p.6200-6205
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2850718241
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T01%3A46%3A07IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Photocatalytic%20Hydro%20Tri/Difluoromethylation%20of%20Alkenes%20with%20Bench%20Stable%20Tri/Difluoromethylating%20Reagents&rft.jtitle=Organic%20letters&rft.au=Yedase,%20Girish%20Suresh&rft.date=2023-08-25&rft.volume=25&rft.issue=33&rft.spage=6200&rft.epage=6205&rft.pages=6200-6205&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.3c02413&rft_dat=%3Cproquest_cross%3E2850718241%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a345t-62e21193172798a5f8fa140968a1baebe257991f68f3533a46272bf48af6f24b3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2850718241&rft_id=info:pmid/37578816&rfr_iscdi=true