Metal-free oxidative coupling of arylmethylamines with indoles: a simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes
The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant. The present reaction provides a novel route towards the synthesis of 3,3′-bis(indolyl)methanes in excellent yields of up to 95% via C-C and C-N bond formation. T...
Gespeichert in:
| Veröffentlicht in: | RSC advances 2020-06, Vol.1 (39), p.23254-23262 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 23262 |
|---|---|
| container_issue | 39 |
| container_start_page | 23254 |
| container_title | RSC advances |
| container_volume | 1 |
| creator | Kadu, Vikas D Chandrudu, Sankala Naga Hublikar, Mahesh G Raut, Dattatraya G Bhosale, Raghunath B |
| description | The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant. The present reaction provides a novel route towards the synthesis of 3,3′-bis(indolyl)methanes in excellent yields of up to 95%
via
C-C and C-N bond formation. This attractive and environmentally friendly one-pot protocol is a simple procedure that features inexpensive acetic acid as the catalyst and molecular oxygen as the sole oxidant, and it supports a wide substrate scope with the good tolerance of functional groups.
The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant towards a novel rout of 3,3′-bis(indolyl)methanes (BIMs) synthesis. |
| doi_str_mv | 10.1039/d0ra03221b |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_rsc_primary_d0ra03221b</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2414741039</sourcerecordid><originalsourceid>FETCH-LOGICAL-c454t-28be18f5c5a58e717717a44a27b0a67c815d4c2b5bb2b28c45aaf8733e76f05b3</originalsourceid><addsrcrecordid>eNp9ks1u1DAQxyMEolXphTvIiEtBDfgzznJAKuVTKkJCcLbsZLLryrFTO1nIjefgMXgkngRvtyyFA5alGen_839mNC6KuwQ_IZgtnrY4aswoJeZGsU8xr0qKq8XNa_lecZjSOc6nEoRW5Haxx4SgmDG5X3x_D6N2ZRcBUPhqWz3aNaAmTIOzfolCh3ScXQ_jana6tx4S-mLHFbK-DQ7SM6RRsv3g4BiBX9sYfA8-O7oZGfB26ZEehhh0s0JdiGhcAUqzzyHZtHFnx-zntx-lseno0nJ2jzbFdC50p7jVaZfg8CoeFJ9fv_p0-rY8-_Dm3enJWdlwwceS1gZI3YlGaFGDJDJfzbmm0mBdyaYmouUNNcIYamidH2nd1ZIxkFWHhWEHxfOt7zCZHtom9x-1U0O0fZ5dBW3V34q3K7UMa7XAgksqs8HRlUEMFxOkUfU2NeBcniJMSdGqIrimFa8z-vAf9DxM0efxFOWES77ZaaYeb6kmhpQidLtmCFYbQr3EH08ut_4iw_evt79Df-84A_e2QEzNTv3zbbL-4H-6GtqO_QLWkMD8</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2414741039</pqid></control><display><type>article</type><title>Metal-free oxidative coupling of arylmethylamines with indoles: a simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central</source><source>PubMed Central Open Access</source><creator>Kadu, Vikas D ; Chandrudu, Sankala Naga ; Hublikar, Mahesh G ; Raut, Dattatraya G ; Bhosale, Raghunath B</creator><creatorcontrib>Kadu, Vikas D ; Chandrudu, Sankala Naga ; Hublikar, Mahesh G ; Raut, Dattatraya G ; Bhosale, Raghunath B</creatorcontrib><description>The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant. The present reaction provides a novel route towards the synthesis of 3,3′-bis(indolyl)methanes in excellent yields of up to 95%
via
C-C and C-N bond formation. This attractive and environmentally friendly one-pot protocol is a simple procedure that features inexpensive acetic acid as the catalyst and molecular oxygen as the sole oxidant, and it supports a wide substrate scope with the good tolerance of functional groups.
The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant towards a novel rout of 3,3′-bis(indolyl)methanes (BIMs) synthesis.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d0ra03221b</identifier><identifier>PMID: 35520337</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Acetic acid ; Chemistry ; Coupling (molecular) ; Functional groups ; Indoles ; Oxidizing agents ; Oxygen ; Substrates</subject><ispartof>RSC advances, 2020-06, Vol.1 (39), p.23254-23262</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2020</rights><rights>This journal is © The Royal Society of Chemistry 2020 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c454t-28be18f5c5a58e717717a44a27b0a67c815d4c2b5bb2b28c45aaf8733e76f05b3</citedby><cites>FETCH-LOGICAL-c454t-28be18f5c5a58e717717a44a27b0a67c815d4c2b5bb2b28c45aaf8733e76f05b3</cites><orcidid>0000-0001-8116-4290 ; 0000-0001-7286-093X ; 0000-0003-1442-9206</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054727/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054727/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35520337$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kadu, Vikas D</creatorcontrib><creatorcontrib>Chandrudu, Sankala Naga</creatorcontrib><creatorcontrib>Hublikar, Mahesh G</creatorcontrib><creatorcontrib>Raut, Dattatraya G</creatorcontrib><creatorcontrib>Bhosale, Raghunath B</creatorcontrib><title>Metal-free oxidative coupling of arylmethylamines with indoles: a simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant. The present reaction provides a novel route towards the synthesis of 3,3′-bis(indolyl)methanes in excellent yields of up to 95%
via
C-C and C-N bond formation. This attractive and environmentally friendly one-pot protocol is a simple procedure that features inexpensive acetic acid as the catalyst and molecular oxygen as the sole oxidant, and it supports a wide substrate scope with the good tolerance of functional groups.
The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant towards a novel rout of 3,3′-bis(indolyl)methanes (BIMs) synthesis.</description><subject>Acetic acid</subject><subject>Chemistry</subject><subject>Coupling (molecular)</subject><subject>Functional groups</subject><subject>Indoles</subject><subject>Oxidizing agents</subject><subject>Oxygen</subject><subject>Substrates</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9ks1u1DAQxyMEolXphTvIiEtBDfgzznJAKuVTKkJCcLbsZLLryrFTO1nIjefgMXgkngRvtyyFA5alGen_839mNC6KuwQ_IZgtnrY4aswoJeZGsU8xr0qKq8XNa_lecZjSOc6nEoRW5Haxx4SgmDG5X3x_D6N2ZRcBUPhqWz3aNaAmTIOzfolCh3ScXQ_jana6tx4S-mLHFbK-DQ7SM6RRsv3g4BiBX9sYfA8-O7oZGfB26ZEehhh0s0JdiGhcAUqzzyHZtHFnx-zntx-lseno0nJ2jzbFdC50p7jVaZfg8CoeFJ9fv_p0-rY8-_Dm3enJWdlwwceS1gZI3YlGaFGDJDJfzbmm0mBdyaYmouUNNcIYamidH2nd1ZIxkFWHhWEHxfOt7zCZHtom9x-1U0O0fZ5dBW3V34q3K7UMa7XAgksqs8HRlUEMFxOkUfU2NeBcniJMSdGqIrimFa8z-vAf9DxM0efxFOWES77ZaaYeb6kmhpQidLtmCFYbQr3EH08ut_4iw_evt79Df-84A_e2QEzNTv3zbbL-4H-6GtqO_QLWkMD8</recordid><startdate>20200617</startdate><enddate>20200617</enddate><creator>Kadu, Vikas D</creator><creator>Chandrudu, Sankala Naga</creator><creator>Hublikar, Mahesh G</creator><creator>Raut, Dattatraya G</creator><creator>Bhosale, Raghunath B</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-8116-4290</orcidid><orcidid>https://orcid.org/0000-0001-7286-093X</orcidid><orcidid>https://orcid.org/0000-0003-1442-9206</orcidid></search><sort><creationdate>20200617</creationdate><title>Metal-free oxidative coupling of arylmethylamines with indoles: a simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes</title><author>Kadu, Vikas D ; Chandrudu, Sankala Naga ; Hublikar, Mahesh G ; Raut, Dattatraya G ; Bhosale, Raghunath B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c454t-28be18f5c5a58e717717a44a27b0a67c815d4c2b5bb2b28c45aaf8733e76f05b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Acetic acid</topic><topic>Chemistry</topic><topic>Coupling (molecular)</topic><topic>Functional groups</topic><topic>Indoles</topic><topic>Oxidizing agents</topic><topic>Oxygen</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kadu, Vikas D</creatorcontrib><creatorcontrib>Chandrudu, Sankala Naga</creatorcontrib><creatorcontrib>Hublikar, Mahesh G</creatorcontrib><creatorcontrib>Raut, Dattatraya G</creatorcontrib><creatorcontrib>Bhosale, Raghunath B</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kadu, Vikas D</au><au>Chandrudu, Sankala Naga</au><au>Hublikar, Mahesh G</au><au>Raut, Dattatraya G</au><au>Bhosale, Raghunath B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-free oxidative coupling of arylmethylamines with indoles: a simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2020-06-17</date><risdate>2020</risdate><volume>1</volume><issue>39</issue><spage>23254</spage><epage>23262</epage><pages>23254-23262</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant. The present reaction provides a novel route towards the synthesis of 3,3′-bis(indolyl)methanes in excellent yields of up to 95%
via
C-C and C-N bond formation. This attractive and environmentally friendly one-pot protocol is a simple procedure that features inexpensive acetic acid as the catalyst and molecular oxygen as the sole oxidant, and it supports a wide substrate scope with the good tolerance of functional groups.
The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant towards a novel rout of 3,3′-bis(indolyl)methanes (BIMs) synthesis.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35520337</pmid><doi>10.1039/d0ra03221b</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-8116-4290</orcidid><orcidid>https://orcid.org/0000-0001-7286-093X</orcidid><orcidid>https://orcid.org/0000-0003-1442-9206</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2046-2069 |
| ispartof | RSC advances, 2020-06, Vol.1 (39), p.23254-23262 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_rsc_primary_d0ra03221b |
| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Acetic acid Chemistry Coupling (molecular) Functional groups Indoles Oxidizing agents Oxygen Substrates |
| title | Metal-free oxidative coupling of arylmethylamines with indoles: a simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-28T13%3A40%3A53IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_rsc_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Metal-free%20oxidative%20coupling%20of%20arylmethylamines%20with%20indoles:%20a%20simple,%20environmentally%20benign%20approach%20for%20the%20synthesis%20of%203,3%E2%80%B2-bis(indolyl)methanes&rft.jtitle=RSC%20advances&rft.au=Kadu,%20Vikas%20D&rft.date=2020-06-17&rft.volume=1&rft.issue=39&rft.spage=23254&rft.epage=23262&rft.pages=23254-23262&rft.issn=2046-2069&rft.eissn=2046-2069&rft_id=info:doi/10.1039/d0ra03221b&rft_dat=%3Cproquest_rsc_p%3E2414741039%3C/proquest_rsc_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2414741039&rft_id=info:pmid/35520337&rfr_iscdi=true |