Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl–Alkyl Cross-Couplings
A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl–alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react wi...
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| Published in | Journal of the American Chemical Society Vol. 141; no. 6; pp. 2257 - 2262 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
13.02.2019
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl–alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the noncanonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance. |
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| AbstractList | A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl–alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the noncanonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance. A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl–alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the noncanonical transformation of NH₂ groups into a wide range of alkyl substituents with broad functional group tolerance. A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl-alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the non-canonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance. A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl-alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the noncanonical transformation of NH groups into a wide range of alkyl substituents with broad functional group tolerance. A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl-alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the noncanonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance.A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl-alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the noncanonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance. |
| Author | Plunkett, Shane Watson, Mary P Santana, Samantha O Basch, Corey H |
| AuthorAffiliation | Department of Chemistry & Biochemistry |
| AuthorAffiliation_xml | – name: Department of Chemistry & Biochemistry |
| Author_xml | – sequence: 1 givenname: Shane surname: Plunkett fullname: Plunkett, Shane – sequence: 2 givenname: Corey H surname: Basch fullname: Basch, Corey H – sequence: 3 givenname: Samantha O surname: Santana fullname: Santana, Samantha O – sequence: 4 givenname: Mary P orcidid: 0000-0002-1879-5257 surname: Watson fullname: Watson, Mary P email: mpwatson@udel.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30682254$$D View this record in MEDLINE/PubMed |
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| Keywords | BORONIC ACIDS AMINO-GROUPS ESTERS BOND FUNCTIONALIZATION SECONDARY ARYL PYRIDINIUM SALTS BENZYLIC AMMONIUM-SALTS NICKEL-CATALYZED BORYLATION CARBOXYLIC-ACIDS |
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| Snippet | A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl–alkyl bond formation via... A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl-alkyl bond formation via... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary cross-coupling reactions halides Lewis acids moieties Physical Sciences primary amines Science & Technology |
| Title | Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl–Alkyl Cross-Couplings |
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