Dehydrogenative C(sp)-H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions
The organocatalyzed Mannich reaction of unsubstituted and N -aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several N -aryl-substituted THIQs through dehydrogenative C(sp3)-H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron ox...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2019-07, Vol.17 (26), p.642-6425 |
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| container_title | Organic & biomolecular chemistry |
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| creator | D ambaski, Zdravko Bond i, Bojan P |
| description | The organocatalyzed Mannich reaction of unsubstituted and
N
-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several
N
-aryl-substituted THIQs through dehydrogenative C(sp3)-H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C-H oxidation/Mannich reaction of less reactive
N
-aryl substituted pyrrolidines is achieved
via
metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.
DDQ and IBX are effective SET oxidants of
N
-aryl-protected and unprotected THIQs. Mannich and Strecker type functionalizations ensued in an overall CDC reaction. |
| doi_str_mv | 10.1039/c9ob01090d |
| format | Article |
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N
-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several
N
-aryl-substituted THIQs through dehydrogenative C(sp3)-H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C-H oxidation/Mannich reaction of less reactive
N
-aryl substituted pyrrolidines is achieved
via
metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.
DDQ and IBX are effective SET oxidants of
N
-aryl-protected and unprotected THIQs. Mannich and Strecker type functionalizations ensued in an overall CDC reaction.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c9ob01090d</identifier><identifier>PMID: 31225575</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Catalysis ; Dehydrogenation ; Hydrogen bonds ; Oxidants ; Oxidation ; Oxidizing agents ; Photoredox catalysis ; Single electrons ; Substitutes</subject><ispartof>Organic & biomolecular chemistry, 2019-07, Vol.17 (26), p.642-6425</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-70c76311578deaa061498542aeca61883cb1f171afbc2b0ef6bce9a9db0b39f23</citedby><cites>FETCH-LOGICAL-c363t-70c76311578deaa061498542aeca61883cb1f171afbc2b0ef6bce9a9db0b39f23</cites><orcidid>0000-0002-8249-6091</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27929,27930</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31225575$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>D ambaski, Zdravko</creatorcontrib><creatorcontrib>Bond i, Bojan P</creatorcontrib><title>Dehydrogenative C(sp)-H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>The organocatalyzed Mannich reaction of unsubstituted and
N
-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several
N
-aryl-substituted THIQs through dehydrogenative C(sp3)-H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C-H oxidation/Mannich reaction of less reactive
N
-aryl substituted pyrrolidines is achieved
via
metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.
DDQ and IBX are effective SET oxidants of
N
-aryl-protected and unprotected THIQs. Mannich and Strecker type functionalizations ensued in an overall CDC reaction.</description><subject>Aromatic compounds</subject><subject>Catalysis</subject><subject>Dehydrogenation</subject><subject>Hydrogen bonds</subject><subject>Oxidants</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Photoredox catalysis</subject><subject>Single electrons</subject><subject>Substitutes</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kc1P3DAQxa2qVYFtL9xbGXGhSGntOHbiIyxQkJC4tOfIH2MwytpbO6m6iD8eLwtbqYeeZqT3m6fRewjtU_KVEia_GRk1oUQS-wbt0qZtK8KZfLvda7KD9nK-J4TKVjTv0Q6jdc15y3fR4xncrWyKtxDU6H8Dnh_l5ZfqEusYLHZTMKOPQQ3-Qa0XHB0eYUzq-cjn-GvyIQ4-QMYLsF6NYLFe4ZhuVfAGxz_eqjBmPAULCS_8YLEpzn5tlj-gd04NGT6-zBn6eXH-Y35ZXd98v5qfXFeGCTZWLTGtYJTytrOgFBG0kR1vagVGCdp1zGjqaEuV06bWBJzQBqSSVhPNpKvZDB1tfJepPAx57Bc-GxgGFSBOua_rhouGCcELevgPeh-nVAJYU5zIjnUl8xk63lAmxZwTuH6Z_EKlVU9Jv-6kn8ub0-dOzgr8-cVy0iWjLfpaQgE-bYCUzVb9W2rRD_6n90vr2BOndJ5-</recordid><startdate>20190714</startdate><enddate>20190714</enddate><creator>D ambaski, Zdravko</creator><creator>Bond i, Bojan P</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8249-6091</orcidid></search><sort><creationdate>20190714</creationdate><title>Dehydrogenative C(sp)-H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions</title><author>D ambaski, Zdravko ; Bond i, Bojan P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-70c76311578deaa061498542aeca61883cb1f171afbc2b0ef6bce9a9db0b39f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aromatic compounds</topic><topic>Catalysis</topic><topic>Dehydrogenation</topic><topic>Hydrogen bonds</topic><topic>Oxidants</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Photoredox catalysis</topic><topic>Single electrons</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>D ambaski, Zdravko</creatorcontrib><creatorcontrib>Bond i, Bojan P</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>D ambaski, Zdravko</au><au>Bond i, Bojan P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dehydrogenative C(sp)-H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2019-07-14</date><risdate>2019</risdate><volume>17</volume><issue>26</issue><spage>642</spage><epage>6425</epage><pages>642-6425</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The organocatalyzed Mannich reaction of unsubstituted and
N
-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several
N
-aryl-substituted THIQs through dehydrogenative C(sp3)-H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C-H oxidation/Mannich reaction of less reactive
N
-aryl substituted pyrrolidines is achieved
via
metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.
DDQ and IBX are effective SET oxidants of
N
-aryl-protected and unprotected THIQs. Mannich and Strecker type functionalizations ensued in an overall CDC reaction.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>31225575</pmid><doi>10.1039/c9ob01090d</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-8249-6091</orcidid></addata></record> |
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| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2019-07, Vol.17 (26), p.642-6425 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_pubmed_primary_31225575 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Aromatic compounds Catalysis Dehydrogenation Hydrogen bonds Oxidants Oxidation Oxidizing agents Photoredox catalysis Single electrons Substitutes |
| title | Dehydrogenative C(sp)-H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions |
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