Three-Component Coupling of Arenes, Ethylene, and Alkynes Catalyzed by a Cationic Bis(phosphine) Cobalt Complex: Intercepting Metallacyclopentenes for C–H Functionalization

A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis­(phosphine) cobalt­(I) complex, [(dcype)­Co­(η6-C7H8)]­[BArF 4] (dcype = 1,2-bis­(dicyclohexylphosphino)­ethane; BArF 4 = B­[(3,5-(CF3)2)­C6H3]4),...

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Published inJournal of the American Chemical Society Vol. 144; no. 10; pp. 4530 - 4540
Main Authors Whitehurst, William G, Kim, Junho, Koenig, Stefan G, Chirik, Paul J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.03.2022
Amer Chemical Soc
Subjects
Alkynes
aromatic hydrocarbons
carbon-hydrogen bond activation
Catalysis
Cations
Chemistry
Chemistry, Multidisciplinary
Cobalt
deuterium
ethane
ethylene
Ethylenes
fenofibrate
haloperidol
Molecular Structure
phosphine
Phosphines
Physical Sciences
Science & Technology
ALKENES
CYCLOADDITION
ACTIVATION
1,6-ENYNES
HYDROBORATION/CYCLIZATION
N-H
METAL
HYDROARYLATIONS
METALLOCYCLES
ENYNES
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Abstract A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis­(phosphine) cobalt­(I) complex, [(dcype)­Co­(η6-C7H8)]­[BArF 4] (dcype = 1,2-bis­(dicyclohexylphosphino)­ethane; BArF 4 = B­[(3,5-(CF3)2)­C6H3]4), as the precatalyst. All three components were required for turnover and formation of ortho-homoallylated arene products. A range of directing groups including amide, ketone, and 2-pyridyl substituents on the arene promoted the reaction. The cobalt-catalyzed method exhibited broad functional group tolerance allowing for the late-stage functionalization of two drug molecules, fenofibrate and haloperidol. A series of control reactions, deuterium labeling studies, resting state analysis, as well as synthesis of substrate- and product-bound η6-arene complexes supported a pathway involving C­(sp 2 )–H activation from a cobalt­(III) metallacycle.
AbstractList A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis(phosphine) cobalt(I) complex, [(dcype) Co(eta(6)-C7H8)][BAr4F] (dcype = 1,2-bis(dicyclohexylphosphino)ethane; BAr4F = B[(3,5-(CF3)(2))C6H3](4)), as the precatalyst. All three components were required for turnover and formation of ortho-homoallylated arene products. A range of directing groups including amide, ketone, and 2-pyridyl substituents on the arene promoted the reaction. The cobalt-catalyzed method exhibited broad functional group tolerance allowing for the late-stage functionalization of two drug molecules, fenofibrate and haloperidol. A series of control reactions, deuterium labeling studies, resting state analysis, as well as synthesis of substrate- and product-bound eta(6)-arene complexes supported a pathway involving C(sp(2))-H activation from a cobalt(III) metallacycle.
A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis(phosphine) cobalt(I) complex, [(dcype)Co(η -C H )][BAr ] (dcype = 1,2-bis(dicyclohexylphosphino)ethane; BAr = B[(3,5-(CF ) )C H ] ), as the precatalyst. All three components were required for turnover and formation of -homoallylated arene products. A range of directing groups including amide, ketone, and 2-pyridyl substituents on the arene promoted the reaction. The cobalt-catalyzed method exhibited broad functional group tolerance allowing for the late-stage functionalization of two drug molecules, fenofibrate and haloperidol. A series of control reactions, deuterium labeling studies, resting state analysis, as well as synthesis of substrate- and product-bound η -arene complexes supported a pathway involving C( )-H activation from a cobalt(III) metallacycle.
A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis(phosphine) cobalt(I) complex, [(dcype)Co(η⁶-C₇H₈)][BArF₄] (dcype = 1,2-bis(dicyclohexylphosphino)ethane; BArF₄ = B[(3,5-(CF₃)₂)C₆H₃]₄), as the precatalyst. All three components were required for turnover and formation of ortho-homoallylated arene products. A range of directing groups including amide, ketone, and 2-pyridyl substituents on the arene promoted the reaction. The cobalt-catalyzed method exhibited broad functional group tolerance allowing for the late-stage functionalization of two drug molecules, fenofibrate and haloperidol. A series of control reactions, deuterium labeling studies, resting state analysis, as well as synthesis of substrate- and product-bound η⁶-arene complexes supported a pathway involving C(sp²)–H activation from a cobalt(III) metallacycle.
A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis­(phosphine) cobalt­(I) complex, [(dcype)­Co­(η6-C7H8)]­[BArF 4] (dcype = 1,2-bis­(dicyclohexylphosphino)­ethane; BArF 4 = B­[(3,5-(CF3)2)­C6H3]4), as the precatalyst. All three components were required for turnover and formation of ortho-homoallylated arene products. A range of directing groups including amide, ketone, and 2-pyridyl substituents on the arene promoted the reaction. The cobalt-catalyzed method exhibited broad functional group tolerance allowing for the late-stage functionalization of two drug molecules, fenofibrate and haloperidol. A series of control reactions, deuterium labeling studies, resting state analysis, as well as synthesis of substrate- and product-bound η6-arene complexes supported a pathway involving C­(sp 2 )–H activation from a cobalt­(III) metallacycle.
A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis(phosphine) cobalt(I) complex, [(dcype)Co(η 6 -C 7 H 8 )][BAr F 4 ] (dcype = 1,2-bis(dicyclohexylphosphino)ethane; BAr F 4 = B[(3,5-(CF 3 ) 2 )C 6 H 3 ] 4 ), as the precatalyst. All three components were required for turnover and formation of ortho -homoallylated arene products. A range of directing groups including amide, ketone, and 2-pyridyl substituents on the arene promoted the reaction. The cobalt-catalyzed method exhibited broad functional group tolerance allowing for the late-stage functionalization of two drug molecules, fenofibrate and haloperidol. A series of control reactions, deuterium labeling studies, resting state analysis, as well as synthesis of substrate- and product-bound η 6 -arene complexes supported a pathway involving C( sp 2 )–H activation from a cobalt(III) metallacycle.
A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis(phosphine) cobalt(I) complex, [(dcype)Co(η6-C7H8)][BArF4] (dcype = 1,2-bis(dicyclohexylphosphino)ethane; BArF4 = B[(3,5-(CF3)2)C6H3]4), as the precatalyst. All three components were required for turnover and formation of ortho-homoallylated arene products. A range of directing groups including amide, ketone, and 2-pyridyl substituents on the arene promoted the reaction. The cobalt-catalyzed method exhibited broad functional group tolerance allowing for the late-stage functionalization of two drug molecules, fenofibrate and haloperidol. A series of control reactions, deuterium labeling studies, resting state analysis, as well as synthesis of substrate- and product-bound η6-arene complexes supported a pathway involving C(sp2)-H activation from a cobalt(III) metallacycle.A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic bis(phosphine) cobalt(I) complex, [(dcype)Co(η6-C7H8)][BArF4] (dcype = 1,2-bis(dicyclohexylphosphino)ethane; BArF4 = B[(3,5-(CF3)2)C6H3]4), as the precatalyst. All three components were required for turnover and formation of ortho-homoallylated arene products. A range of directing groups including amide, ketone, and 2-pyridyl substituents on the arene promoted the reaction. The cobalt-catalyzed method exhibited broad functional group tolerance allowing for the late-stage functionalization of two drug molecules, fenofibrate and haloperidol. A series of control reactions, deuterium labeling studies, resting state analysis, as well as synthesis of substrate- and product-bound η6-arene complexes supported a pathway involving C(sp2)-H activation from a cobalt(III) metallacycle.
Author Kim, Junho
Whitehurst, William G
Koenig, Stefan G
Chirik, Paul J
AuthorAffiliation Department of Chemistry, Frick Laboratory
AuthorAffiliation_xml – name: Department of Chemistry, Frick Laboratory
Author_xml – sequence: 1
  givenname: William G
  orcidid: 0000-0001-9789-1265
  surname: Whitehurst
  fullname: Whitehurst, William G
  organization: Department of Chemistry, Frick Laboratory
– sequence: 2
  givenname: Junho
  orcidid: 0000-0002-8977-2925
  surname: Kim
  fullname: Kim, Junho
  organization: Department of Chemistry, Frick Laboratory
– sequence: 3
  givenname: Stefan G
  orcidid: 0000-0002-1878-614X
  surname: Koenig
  fullname: Koenig, Stefan G
  email: koenig.stefan@gene.com
– sequence: 4
  givenname: Paul J
  orcidid: 0000-0001-8473-2898
  surname: Chirik
  fullname: Chirik, Paul J
  email: pchirik@princeton.edu
  organization: Department of Chemistry, Frick Laboratory
BackLink https://www.ncbi.nlm.nih.gov/pubmed/35245039$$D View this record in MEDLINE/PubMed
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Issue 10
Keywords ALKENES
CYCLOADDITION
ACTIVATION
1,6-ENYNES
HYDROBORATION/CYCLIZATION
N-H
METAL
HYDROARYLATIONS
METALLOCYCLES
ENYNES
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Snippet A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic...
A cobalt-catalyzed intermolecular three-component coupling of arenes, ethylene, and alkynes was developed using the well-defined air-stable cationic...
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SubjectTerms Alkynes
aromatic hydrocarbons
carbon-hydrogen bond activation
Catalysis
Cations
Chemistry
Chemistry, Multidisciplinary
Cobalt
deuterium
ethane
ethylene
Ethylenes
fenofibrate
haloperidol
Molecular Structure
phosphine
Phosphines
Physical Sciences
Science & Technology
Title Three-Component Coupling of Arenes, Ethylene, and Alkynes Catalyzed by a Cationic Bis(phosphine) Cobalt Complex: Intercepting Metallacyclopentenes for C–H Functionalization
URI http://dx.doi.org/10.1021/jacs.1c12646
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000776234200029
https://www.ncbi.nlm.nih.gov/pubmed/35245039
https://www.proquest.com/docview/2636147564
https://www.proquest.com/docview/2648853259
https://pubmed.ncbi.nlm.nih.gov/PMC8931730
Volume 144
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