Oxidative additions of alkynyl/vinyl iodides to gold and gold-catalyzed vinylation reactions triggered by the MeDalphos ligand
The hemilabile Ad 2 P( o -C 6 H 4 )NMe 2 ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold. The reaction is general. It works with a broad range of substrates of various electronic bias and steric demand, and proceeds with complete retention...
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| Veröffentlicht in: | Chemical science (Cambridge) 2021-01, Vol.12 (22), p.776-7712 |
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| creator | Rodriguez, Jessica Tabey, Alexis Mallet-Ladeira, Sonia Bourissou, Didier |
| description | The hemilabile Ad
2
P(
o
-C
6
H
4
)NMe
2
ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold. The reaction is general. It works with a broad range of substrates of various electronic bias and steric demand, and proceeds with complete retention of stereochemistry from
Z
and
E
vinyl iodides. Both alkynyl and vinyl iodides react faster than aryl iodides. The elementary step is amenable to catalysis. Oxidative addition of vinyl iodides to gold and π-activation of alkenols (and
N
-alkenyl amines) at gold have been combined to achieve hetero-vinylation reactions. A number of functionalized heterocycles,
i.e.
tetrahydrofuranes, tetrahydropyranes, oxepanes and pyrrolidines were obtained thereby (24 examples, 87% average yield). Taking advantage of the chemoselectivity for vinyl iodides over aryl iodides, sequential transformations involving first a hetero-vinylation step and then a C-N coupling, a C-C coupling or an heteroarylation were achieved from a vinyl/aryl bis-iodide substrate.
The hemilabile Ad
2
P(
o
-C
6
H
4
)NMe
2
ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold. |
| doi_str_mv | 10.1039/d1sc01483h |
| format | Article |
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2
P(
o
-C
6
H
4
)NMe
2
ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold. The reaction is general. It works with a broad range of substrates of various electronic bias and steric demand, and proceeds with complete retention of stereochemistry from
Z
and
E
vinyl iodides. Both alkynyl and vinyl iodides react faster than aryl iodides. The elementary step is amenable to catalysis. Oxidative addition of vinyl iodides to gold and π-activation of alkenols (and
N
-alkenyl amines) at gold have been combined to achieve hetero-vinylation reactions. A number of functionalized heterocycles,
i.e.
tetrahydrofuranes, tetrahydropyranes, oxepanes and pyrrolidines were obtained thereby (24 examples, 87% average yield). Taking advantage of the chemoselectivity for vinyl iodides over aryl iodides, sequential transformations involving first a hetero-vinylation step and then a C-N coupling, a C-C coupling or an heteroarylation were achieved from a vinyl/aryl bis-iodide substrate.
The hemilabile Ad
2
P(
o
-C
6
H
4
)NMe
2
ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d1sc01483h</identifier><identifier>PMID: 34168822</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Amines ; Aromatic compounds ; Catalysis ; Chemical reactions ; Chemical Sciences ; Chemistry ; Coupling ; Crystallography ; Gold ; Iodides ; Ligands ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Stereochemistry ; Substrates</subject><ispartof>Chemical science (Cambridge), 2021-01, Vol.12 (22), p.776-7712</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><rights>This journal is © The Royal Society of Chemistry 2021 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c505t-9e934c95910c7fc8e3dc74d8b66de882e8e03be690b1dd8c0bd59c476af987743</citedby><cites>FETCH-LOGICAL-c505t-9e934c95910c7fc8e3dc74d8b66de882e8e03be690b1dd8c0bd59c476af987743</cites><orcidid>0000-0002-6960-3542 ; 0000-0002-3814-6588 ; 0000-0002-0249-1769 ; 0009-0004-2446-6697</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/PMC8188461/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8188461/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03430303$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Rodriguez, Jessica</creatorcontrib><creatorcontrib>Tabey, Alexis</creatorcontrib><creatorcontrib>Mallet-Ladeira, Sonia</creatorcontrib><creatorcontrib>Bourissou, Didier</creatorcontrib><title>Oxidative additions of alkynyl/vinyl iodides to gold and gold-catalyzed vinylation reactions triggered by the MeDalphos ligand</title><title>Chemical science (Cambridge)</title><description>The hemilabile Ad
2
P(
o
-C
6
H
4
)NMe
2
ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold. The reaction is general. It works with a broad range of substrates of various electronic bias and steric demand, and proceeds with complete retention of stereochemistry from
Z
and
E
vinyl iodides. Both alkynyl and vinyl iodides react faster than aryl iodides. The elementary step is amenable to catalysis. Oxidative addition of vinyl iodides to gold and π-activation of alkenols (and
N
-alkenyl amines) at gold have been combined to achieve hetero-vinylation reactions. A number of functionalized heterocycles,
i.e.
tetrahydrofuranes, tetrahydropyranes, oxepanes and pyrrolidines were obtained thereby (24 examples, 87% average yield). Taking advantage of the chemoselectivity for vinyl iodides over aryl iodides, sequential transformations involving first a hetero-vinylation step and then a C-N coupling, a C-C coupling or an heteroarylation were achieved from a vinyl/aryl bis-iodide substrate.
The hemilabile Ad
2
P(
o
-C
6
H
4
)NMe
2
ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold.</description><subject>Amines</subject><subject>Aromatic compounds</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Coupling</subject><subject>Crystallography</subject><subject>Gold</subject><subject>Iodides</subject><subject>Ligands</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Stereochemistry</subject><subject>Substrates</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdksFu3CAQhq2qVROlufReCamXppITMNiGS6Vo03YjbZRD2zPCMLZJWbMF76ruoc9edh1tlYDEjJhvfmCYLHtL8CXBVFwZEjUmjNP-RXZaYEbyqqTi5dEv8El2HuMDToNSUhb16-yEMlJxXhSn2d_739ao0e4AKWPsaP0QkW-Rcj-nYXJXO5tWZL2xBiIaPeq8M0gN5uDkWo3KTX_AoAOo9vkogNKz0Bhs10FI4WZCYw_oDm6U2_Q-Ime7pPIme9UqF-H80Z5lP758_r5Y5qv7r7eL61WuS1yOuQBBmRalIFjXreZAja6Z4U1VGUgPAQ6YNlAJ3BBjuMaNKYVmdaVaweua0bPs06y72TZrMBqGMSgnN8GuVZikV1Y-jQy2l53fSU44ZxVJAhezQP8sbXm9kvs9TBnFae727IfHw4L_tYU4yrWNGpxTA_htlEXJylLUqf4Jff8MffDbMKRSJIoKzET6sUR9nCkdfIwB2uMNCJb7LpA35Nvi0AXLBL-b4RD1kfvfJfQfhWCu0A</recordid><startdate>20210101</startdate><enddate>20210101</enddate><creator>Rodriguez, Jessica</creator><creator>Tabey, Alexis</creator><creator>Mallet-Ladeira, Sonia</creator><creator>Bourissou, Didier</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-6960-3542</orcidid><orcidid>https://orcid.org/0000-0002-3814-6588</orcidid><orcidid>https://orcid.org/0000-0002-0249-1769</orcidid><orcidid>https://orcid.org/0009-0004-2446-6697</orcidid></search><sort><creationdate>20210101</creationdate><title>Oxidative additions of alkynyl/vinyl iodides to gold and gold-catalyzed vinylation reactions triggered by the MeDalphos ligand</title><author>Rodriguez, Jessica ; Tabey, Alexis ; Mallet-Ladeira, Sonia ; Bourissou, Didier</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c505t-9e934c95910c7fc8e3dc74d8b66de882e8e03be690b1dd8c0bd59c476af987743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amines</topic><topic>Aromatic compounds</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Coupling</topic><topic>Crystallography</topic><topic>Gold</topic><topic>Iodides</topic><topic>Ligands</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Stereochemistry</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rodriguez, Jessica</creatorcontrib><creatorcontrib>Tabey, Alexis</creatorcontrib><creatorcontrib>Mallet-Ladeira, Sonia</creatorcontrib><creatorcontrib>Bourissou, Didier</creatorcontrib><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>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rodriguez, Jessica</au><au>Tabey, Alexis</au><au>Mallet-Ladeira, Sonia</au><au>Bourissou, Didier</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative additions of alkynyl/vinyl iodides to gold and gold-catalyzed vinylation reactions triggered by the MeDalphos ligand</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2021-01-01</date><risdate>2021</risdate><volume>12</volume><issue>22</issue><spage>776</spage><epage>7712</epage><pages>776-7712</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>The hemilabile Ad
2
P(
o
-C
6
H
4
)NMe
2
ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold. The reaction is general. It works with a broad range of substrates of various electronic bias and steric demand, and proceeds with complete retention of stereochemistry from
Z
and
E
vinyl iodides. Both alkynyl and vinyl iodides react faster than aryl iodides. The elementary step is amenable to catalysis. Oxidative addition of vinyl iodides to gold and π-activation of alkenols (and
N
-alkenyl amines) at gold have been combined to achieve hetero-vinylation reactions. A number of functionalized heterocycles,
i.e.
tetrahydrofuranes, tetrahydropyranes, oxepanes and pyrrolidines were obtained thereby (24 examples, 87% average yield). Taking advantage of the chemoselectivity for vinyl iodides over aryl iodides, sequential transformations involving first a hetero-vinylation step and then a C-N coupling, a C-C coupling or an heteroarylation were achieved from a vinyl/aryl bis-iodide substrate.
The hemilabile Ad
2
P(
o
-C
6
H
4
)NMe
2
ligand promotes fast, quantitative and irreversible oxidative addition of alkynyl and vinyl iodides to gold.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><pmid>34168822</pmid><doi>10.1039/d1sc01483h</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-6960-3542</orcidid><orcidid>https://orcid.org/0000-0002-3814-6588</orcidid><orcidid>https://orcid.org/0000-0002-0249-1769</orcidid><orcidid>https://orcid.org/0009-0004-2446-6697</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2021-01, Vol.12 (22), p.776-7712 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_rsc_primary_d1sc01483h |
| source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| subjects | Amines Aromatic compounds Catalysis Chemical reactions Chemical Sciences Chemistry Coupling Crystallography Gold Iodides Ligands NMR Nuclear magnetic resonance Organic chemistry Stereochemistry Substrates |
| title | Oxidative additions of alkynyl/vinyl iodides to gold and gold-catalyzed vinylation reactions triggered by the MeDalphos ligand |
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