Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines
On the basis of a tandem strategy, AgSbF6/Rh2(OAc)4/Ag3PO4‐mediated reaction of 2‐diazo‐3,5‐dioxo‐6‐ynoate (ynones) with N,N‐disubstituted anilines or aza‐aromatic hydrocarbons afforded a series of 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2‐(4‐aminoaryl or aza‐aryl)‐...
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| Veröffentlicht in: | European journal of organic chemistry 2019-10, Vol.2019 (40), p.6871-6883 |
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| creator | Wan, Yinbo Peng, Haiyun Yang, Qin Liu, Weishun Deng, Guisheng |
| description | On the basis of a tandem strategy, AgSbF6/Rh2(OAc)4/Ag3PO4‐mediated reaction of 2‐diazo‐3,5‐dioxo‐6‐ynoate (ynones) with N,N‐disubstituted anilines or aza‐aromatic hydrocarbons afforded a series of 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2‐(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones). For N‐allyl‐N‐substituted aniline, the corresponding cyclopropanation did not occurred. Disymmetric 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates were also obtained in good yield from 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates and N,N‐disubstituted anilines (or aza‐aromatic hydrocarbons) by C(sp3)–C(sp2) cross‐coupling reaction. AgSbF6/Ag3PO4 plays a key role in the C(sp3)–C(sp2) cross‐coupling reaction. This unique synthetic method for synthesis of two desired products starting from identical materials was proved to be efficient except for N‐substituted aniline.
A novel AgSbF6/Ag3PO4/Rh2(OAc)4‐mediated tandem reaction for selective synthesis of 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2,2‐bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates (or ketones) starting from 2‐diazo‐3,5‐dioxo‐6‐ynoates (ynones) 1 and N,N‐disubstituted aniline was developed. The corresponding cyclopropanation product was not observed when using N‐allyl‐N‐substituted aniline as substrate. |
| doi_str_mv | 10.1002/ejoc.201901342 |
| format | Article |
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A novel AgSbF6/Ag3PO4/Rh2(OAc)4‐mediated tandem reaction for selective synthesis of 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2,2‐bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates (or ketones) starting from 2‐diazo‐3,5‐dioxo‐6‐ynoates (ynones) 1 and N,N‐disubstituted aniline was developed. The corresponding cyclopropanation product was not observed when using N‐allyl‐N‐substituted aniline as substrate.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201901342</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Acetates ; Amines ; Aniline ; Aromatic compounds ; Aromatic hydrocarbons ; Coupling ; Homogeneous catalysis ; Hydrocarbons ; Insertion ; Ketones ; Oxygen heterocycles ; Phosphates ; Silver compounds ; Substitutes ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2019-10, Vol.2019 (40), p.6871-6883</ispartof><rights>2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3172-4dedb9afb4a8f670ed32dc48177f22bfe0085a789660f6a436b9738bf5ae41a93</citedby><cites>FETCH-LOGICAL-c3172-4dedb9afb4a8f670ed32dc48177f22bfe0085a789660f6a436b9738bf5ae41a93</cites><orcidid>0000-0002-6132-5648</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201901342$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201901342$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Wan, Yinbo</creatorcontrib><creatorcontrib>Peng, Haiyun</creatorcontrib><creatorcontrib>Yang, Qin</creatorcontrib><creatorcontrib>Liu, Weishun</creatorcontrib><creatorcontrib>Deng, Guisheng</creatorcontrib><title>Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines</title><title>European journal of organic chemistry</title><description>On the basis of a tandem strategy, AgSbF6/Rh2(OAc)4/Ag3PO4‐mediated reaction of 2‐diazo‐3,5‐dioxo‐6‐ynoate (ynones) with N,N‐disubstituted anilines or aza‐aromatic hydrocarbons afforded a series of 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2‐(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones). For N‐allyl‐N‐substituted aniline, the corresponding cyclopropanation did not occurred. Disymmetric 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates were also obtained in good yield from 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates and N,N‐disubstituted anilines (or aza‐aromatic hydrocarbons) by C(sp3)–C(sp2) cross‐coupling reaction. AgSbF6/Ag3PO4 plays a key role in the C(sp3)–C(sp2) cross‐coupling reaction. This unique synthetic method for synthesis of two desired products starting from identical materials was proved to be efficient except for N‐substituted aniline.
A novel AgSbF6/Ag3PO4/Rh2(OAc)4‐mediated tandem reaction for selective synthesis of 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2,2‐bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates (or ketones) starting from 2‐diazo‐3,5‐dioxo‐6‐ynoates (ynones) 1 and N,N‐disubstituted aniline was developed. The corresponding cyclopropanation product was not observed when using N‐allyl‐N‐substituted aniline as substrate.</description><subject>Acetates</subject><subject>Amines</subject><subject>Aniline</subject><subject>Aromatic compounds</subject><subject>Aromatic hydrocarbons</subject><subject>Coupling</subject><subject>Homogeneous catalysis</subject><subject>Hydrocarbons</subject><subject>Insertion</subject><subject>Ketones</subject><subject>Oxygen heterocycles</subject><subject>Phosphates</subject><subject>Silver compounds</subject><subject>Substitutes</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqNUbtOwzAUtRBIlMLKHImllZriVx4eSykvVeoASGyRk1wLV2lc4hQIE5_Af_EXfAlOi8oIg-9L59xj3YPQMcFDgjE9hbnJhhQTgQnjdAd1CBbCx6HAu67mjPtEsId9dGDtHGMswpB00OctFJDV-hm826asH8Fq6xnl0a_3jx53YbTQpZFVU_Rds50um0qWpnRTmUEta7CeLHOPDlrEmbZrkPwvVVVmsVY81_LNuMwGgYu5Nq9tF7rXuE0ttOeKEmx_LTdyPFnrzGs_CfYQ7SlZWDj6yV10fzG5G1_509nl9Xg09TNGIurzHPJUSJVyGaswwpAzmmc8JlGkKE0VYBwHMordgbAKJWdhKiIWpyqQwIkUrItONnuXlXlaga2TuVlVpZNMKCMkDmIeRg413KCyylhbgUqWlV64cyQEJ61hSWtYsjXMEcSG8KILaP5AJ5Ob2fiX-w3-Eamn</recordid><startdate>20191031</startdate><enddate>20191031</enddate><creator>Wan, Yinbo</creator><creator>Peng, Haiyun</creator><creator>Yang, Qin</creator><creator>Liu, Weishun</creator><creator>Deng, Guisheng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-6132-5648</orcidid></search><sort><creationdate>20191031</creationdate><title>Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines</title><author>Wan, Yinbo ; Peng, Haiyun ; Yang, Qin ; Liu, Weishun ; Deng, Guisheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3172-4dedb9afb4a8f670ed32dc48177f22bfe0085a789660f6a436b9738bf5ae41a93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Acetates</topic><topic>Amines</topic><topic>Aniline</topic><topic>Aromatic compounds</topic><topic>Aromatic hydrocarbons</topic><topic>Coupling</topic><topic>Homogeneous catalysis</topic><topic>Hydrocarbons</topic><topic>Insertion</topic><topic>Ketones</topic><topic>Oxygen heterocycles</topic><topic>Phosphates</topic><topic>Silver compounds</topic><topic>Substitutes</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wan, Yinbo</creatorcontrib><creatorcontrib>Peng, Haiyun</creatorcontrib><creatorcontrib>Yang, Qin</creatorcontrib><creatorcontrib>Liu, Weishun</creatorcontrib><creatorcontrib>Deng, Guisheng</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wan, Yinbo</au><au>Peng, Haiyun</au><au>Yang, Qin</au><au>Liu, Weishun</au><au>Deng, Guisheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines</atitle><jtitle>European journal of organic chemistry</jtitle><date>2019-10-31</date><risdate>2019</risdate><volume>2019</volume><issue>40</issue><spage>6871</spage><epage>6883</epage><pages>6871-6883</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>On the basis of a tandem strategy, AgSbF6/Rh2(OAc)4/Ag3PO4‐mediated reaction of 2‐diazo‐3,5‐dioxo‐6‐ynoate (ynones) with N,N‐disubstituted anilines or aza‐aromatic hydrocarbons afforded a series of 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2‐(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones). For N‐allyl‐N‐substituted aniline, the corresponding cyclopropanation did not occurred. Disymmetric 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates were also obtained in good yield from 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates and N,N‐disubstituted anilines (or aza‐aromatic hydrocarbons) by C(sp3)–C(sp2) cross‐coupling reaction. AgSbF6/Ag3PO4 plays a key role in the C(sp3)–C(sp2) cross‐coupling reaction. This unique synthetic method for synthesis of two desired products starting from identical materials was proved to be efficient except for N‐substituted aniline.
A novel AgSbF6/Ag3PO4/Rh2(OAc)4‐mediated tandem reaction for selective synthesis of 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2,2‐bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates (or ketones) starting from 2‐diazo‐3,5‐dioxo‐6‐ynoates (ynones) 1 and N,N‐disubstituted aniline was developed. The corresponding cyclopropanation product was not observed when using N‐allyl‐N‐substituted aniline as substrate.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201901342</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0002-6132-5648</orcidid></addata></record> |
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| subjects | Acetates Amines Aniline Aromatic compounds Aromatic hydrocarbons Coupling Homogeneous catalysis Hydrocarbons Insertion Ketones Oxygen heterocycles Phosphates Silver compounds Substitutes Synthetic methods |
| title | Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines |
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