Nickel‐Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms
Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N ‐hydroxyphthalimide (NHPI) based redox‐active esters were found to be convenient starting materials for simple, therma...
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| Veröffentlicht in: | Angewandte Chemie 2017-01, Vol.129 (1), p.266-271 |
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| container_title | Angewandte Chemie |
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| creator | Qin, Tian Malins, Lara R. Edwards, Jacob T. Merchant, Rohan R. Novak, Alexander J. E. Zhong, Jacob Z. Mills, Riley B. Yan, Ming Yuan, Changxia Eastgate, Martin D. Baran, Phil S. |
| description | Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition.
N
‐hydroxyphthalimide (NHPI) based redox‐active esters were found to be convenient starting materials for simple, thermal, Ni‐catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH
3
) or an electron‐deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry. |
| doi_str_mv | 10.1002/ange.201609662 |
| format | Article |
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N
‐hydroxyphthalimide (NHPI) based redox‐active esters were found to be convenient starting materials for simple, thermal, Ni‐catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH
3
) or an electron‐deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201609662</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Chemical reactions ; Chemistry ; Conjugates ; Decarboxylation ; Esters ; Hydrogen atoms ; Nickel ; Olefins ; Radicals ; Reagents</subject><ispartof>Angewandte Chemie, 2017-01, Vol.129 (1), p.266-271</ispartof><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1736-3abe8a6a08ec455d86145ac96339d9a2f6c38442d56251c641064c0513c0fb523</citedby><cites>FETCH-LOGICAL-c1736-3abe8a6a08ec455d86145ac96339d9a2f6c38442d56251c641064c0513c0fb523</cites><orcidid>0000-0001-9193-9053</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></links><search><creatorcontrib>Qin, Tian</creatorcontrib><creatorcontrib>Malins, Lara R.</creatorcontrib><creatorcontrib>Edwards, Jacob T.</creatorcontrib><creatorcontrib>Merchant, Rohan R.</creatorcontrib><creatorcontrib>Novak, Alexander J. E.</creatorcontrib><creatorcontrib>Zhong, Jacob Z.</creatorcontrib><creatorcontrib>Mills, Riley B.</creatorcontrib><creatorcontrib>Yan, Ming</creatorcontrib><creatorcontrib>Yuan, Changxia</creatorcontrib><creatorcontrib>Eastgate, Martin D.</creatorcontrib><creatorcontrib>Baran, Phil S.</creatorcontrib><title>Nickel‐Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms</title><title>Angewandte Chemie</title><description>Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition.
N
‐hydroxyphthalimide (NHPI) based redox‐active esters were found to be convenient starting materials for simple, thermal, Ni‐catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH
3
) or an electron‐deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.</description><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Conjugates</subject><subject>Decarboxylation</subject><subject>Esters</subject><subject>Hydrogen atoms</subject><subject>Nickel</subject><subject>Olefins</subject><subject>Radicals</subject><subject>Reagents</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9kc1Kw0AUhQdRsFa3rgfcuEm985uJuxq1CqIidR1uJxNJmyZ1JgXrykfwGX0SEyouXLi6nMvH4cBHyDGDEQPgZ1i_uBEHpiHRmu-QAVOcRSJW8S4ZAEgZGS6TfXIQwhwANI-TAXH3pV246uvjM8UWq827y-kF-rap6aWz6GfN26bCtuwy1jmdlC44-uTQ9q9wTsf00ffBYkWnuHC0A9MKQygtnXqsQ9H4ZTgkewVWwR393CF5vr6apjfR3cPkNh3fRZbFQkcCZ86gRjDOSqVyo5lUaBMtRJInyAtthZGS50pzxayWDLS0oJiwUMwUF0Nyuu1d-eZ17UKbLctgXVVh7Zp1yJiJk8QYkLpDT_6g82bt625dxrt6poBJ8x_FjBI8VkzLjhptKeubELwrspUvl-g3GYOsd5P1brJfN-IbtxCAvQ</recordid><startdate>20170102</startdate><enddate>20170102</enddate><creator>Qin, Tian</creator><creator>Malins, Lara R.</creator><creator>Edwards, Jacob T.</creator><creator>Merchant, Rohan R.</creator><creator>Novak, Alexander J. E.</creator><creator>Zhong, Jacob Z.</creator><creator>Mills, Riley B.</creator><creator>Yan, Ming</creator><creator>Yuan, Changxia</creator><creator>Eastgate, Martin D.</creator><creator>Baran, Phil S.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-9193-9053</orcidid></search><sort><creationdate>20170102</creationdate><title>Nickel‐Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms</title><author>Qin, Tian ; Malins, Lara R. ; Edwards, Jacob T. ; Merchant, Rohan R. ; Novak, Alexander J. E. ; Zhong, Jacob Z. ; Mills, Riley B. ; Yan, Ming ; Yuan, Changxia ; Eastgate, Martin D. ; Baran, Phil S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1736-3abe8a6a08ec455d86145ac96339d9a2f6c38442d56251c641064c0513c0fb523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Conjugates</topic><topic>Decarboxylation</topic><topic>Esters</topic><topic>Hydrogen atoms</topic><topic>Nickel</topic><topic>Olefins</topic><topic>Radicals</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qin, Tian</creatorcontrib><creatorcontrib>Malins, Lara R.</creatorcontrib><creatorcontrib>Edwards, Jacob T.</creatorcontrib><creatorcontrib>Merchant, Rohan R.</creatorcontrib><creatorcontrib>Novak, Alexander J. E.</creatorcontrib><creatorcontrib>Zhong, Jacob Z.</creatorcontrib><creatorcontrib>Mills, Riley B.</creatorcontrib><creatorcontrib>Yan, Ming</creatorcontrib><creatorcontrib>Yuan, Changxia</creatorcontrib><creatorcontrib>Eastgate, Martin D.</creatorcontrib><creatorcontrib>Baran, Phil S.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qin, Tian</au><au>Malins, Lara R.</au><au>Edwards, Jacob T.</au><au>Merchant, Rohan R.</au><au>Novak, Alexander J. E.</au><au>Zhong, Jacob Z.</au><au>Mills, Riley B.</au><au>Yan, Ming</au><au>Yuan, Changxia</au><au>Eastgate, Martin D.</au><au>Baran, Phil S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nickel‐Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms</atitle><jtitle>Angewandte Chemie</jtitle><date>2017-01-02</date><risdate>2017</risdate><volume>129</volume><issue>1</issue><spage>266</spage><epage>271</epage><pages>266-271</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition.
N
‐hydroxyphthalimide (NHPI) based redox‐active esters were found to be convenient starting materials for simple, thermal, Ni‐catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH
3
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| language | eng |
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| source | Access via Wiley Online Library |
| subjects | Chemical reactions Chemistry Conjugates Decarboxylation Esters Hydrogen atoms Nickel Olefins Radicals Reagents |
| title | Nickel‐Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms |
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