Nickel-catalyzed enantioselective arylation of pyridine

J. Patrick Lutz; Stephen T. Chau; Abigail G. Doyle

doi:10.1039/c6sc00702c

Nickel-catalyzed enantioselective arylation of pyridine

J. Patrick Lutz, Stephen T. Chau, Abigail G. Doyle

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75 Scopus citations

Abstract

We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridinium ions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.

Original language	English (US)
Pages (from-to)	4105-4109
Number of pages	5
Journal	Chemical Science
Volume	7
Issue number	7
DOIs	https://doi.org/10.1039/c6sc00702c
State	Published - 2016

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1039/c6sc00702c

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title = "Nickel-catalyzed enantioselective arylation of pyridine",

abstract = "We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridinium ions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.",

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note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

doi = "10.1039/c6sc00702c",

language = "English (US)",

volume = "7",

pages = "4105--4109",

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T1 - Nickel-catalyzed enantioselective arylation of pyridine

AU - Lutz, J. Patrick

AU - Chau, Stephen T.

AU - Doyle, Abigail G.

N1 - Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016

Y1 - 2016

N2 - We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridinium ions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.

AB - We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridinium ions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.

UR - https://www.scopus.com/pages/publications/84976412241

UR - https://www.scopus.com/inward/citedby.url?scp=84976412241&partnerID=8YFLogxK

U2 - 10.1039/c6sc00702c

DO - 10.1039/c6sc00702c

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AN - SCOPUS:84976412241

SN - 2041-6520

VL - 7

SP - 4105

EP - 4109

JO - Chemical Science

JF - Chemical Science

IS - 7

ER -

Nickel-catalyzed enantioselective arylation of pyridine

Abstract

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