Bis(pinacolato)diboron‐Enabled Ni‐Catalyzed Reductive Arylation/Vinylation of Alkyl Electrophiles

Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non‐metallic reductant in mediating Ni‐catalyzed C(sp3)–C(sp2) reductive cross‐coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for hetero...

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Published inAdvanced science Vol. 11; no. 31; pp. e2404301 - n/a
Main Authors Sun, Deli, Gong, Yuxin, Wu, Yu, Chen, Yunrong, Gong, Hegui
Format Journal Article
LanguageEnglish
Published Germany John Wiley & Sons, Inc 01.08.2024
John Wiley and Sons Inc
Wiley
Subjects
Alcohol
cross‐coupling
diboron
electrophile
Hydrocarbons
Ligands
nickel
reductant
Solvents
electrophile
nickel
diboron
cross‐coupling
reductant
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Abstract Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non‐metallic reductant in mediating Ni‐catalyzed C(sp3)–C(sp2) reductive cross‐coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono‐functionalization of diols and bio‐relevant alcohols (e.g., carbohydrates). The use of B2Pin2 shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross‐electrophile coupling chemistry that B2Pin2 can sever as a reductant to reduce NiII to Ni0. This mechanistic insight may inspire the development of new reductive bond‐forming methodologies that can otherwise be difficult to achieve with a metal reductant. The use of economic bis(pinacolato)diboron as the non‐metal reductant to direct the Ni‐catalyzed reductive arylation and vinylation of alkyl halides/ Katritzky salts with the C(sp2)–halides are achieved, which is characteristic of easy removal of boron residue and homogeneous nature of the reaction that are critical concerns for large‐scale and eco‐friendly process chemistry.
AbstractList Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non-metallic reductant in mediating Ni-catalyzed C(sp3)-C(sp2) reductive cross-coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono-functionalization of diols and bio-relevant alcohols (e.g., carbohydrates). The use of B2Pin2 shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross-electrophile coupling chemistry that B2Pin2 can sever as a reductant to reduce NiII to Ni0. This mechanistic insight may inspire the development of new reductive bond-forming methodologies that can otherwise be difficult to achieve with a metal reductant.Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non-metallic reductant in mediating Ni-catalyzed C(sp3)-C(sp2) reductive cross-coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono-functionalization of diols and bio-relevant alcohols (e.g., carbohydrates). The use of B2Pin2 shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross-electrophile coupling chemistry that B2Pin2 can sever as a reductant to reduce NiII to Ni0. This mechanistic insight may inspire the development of new reductive bond-forming methodologies that can otherwise be difficult to achieve with a metal reductant.
Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non‐metallic reductant in mediating Ni‐catalyzed C(sp3)–C(sp2) reductive cross‐coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono‐functionalization of diols and bio‐relevant alcohols (e.g., carbohydrates). The use of B2Pin2 shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross‐electrophile coupling chemistry that B2Pin2 can sever as a reductant to reduce NiII to Ni0. This mechanistic insight may inspire the development of new reductive bond‐forming methodologies that can otherwise be difficult to achieve with a metal reductant. The use of economic bis(pinacolato)diboron as the non‐metal reductant to direct the Ni‐catalyzed reductive arylation and vinylation of alkyl halides/ Katritzky salts with the C(sp2)–halides are achieved, which is characteristic of easy removal of boron residue and homogeneous nature of the reaction that are critical concerns for large‐scale and eco‐friendly process chemistry.
Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B 2 Pin 2 ) is described as a non‐metallic reductant in mediating Ni‐catalyzed C(sp 3 )–C(sp 2 ) reductive cross‐coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono‐functionalization of diols and bio‐relevant alcohols (e.g., carbohydrates). The use of B 2 Pin 2 shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross‐electrophile coupling chemistry that B 2 Pin 2 can sever as a reductant to reduce Ni II to Ni 0 . This mechanistic insight may inspire the development of new reductive bond‐forming methodologies that can otherwise be difficult to achieve with a metal reductant.
Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non‐metallic reductant in mediating Ni‐catalyzed C(sp3)–C(sp2) reductive cross‐coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono‐functionalization of diols and bio‐relevant alcohols (e.g., carbohydrates). The use of B2Pin2 shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross‐electrophile coupling chemistry that B2Pin2 can sever as a reductant to reduce NiII to Ni0. This mechanistic insight may inspire the development of new reductive bond‐forming methodologies that can otherwise be difficult to achieve with a metal reductant.
Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B Pin ) is described as a non-metallic reductant in mediating Ni-catalyzed C(sp )-C(sp ) reductive cross-coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono-functionalization of diols and bio-relevant alcohols (e.g., carbohydrates). The use of B Pin shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross-electrophile coupling chemistry that B Pin can sever as a reductant to reduce Ni to Ni . This mechanistic insight may inspire the development of new reductive bond-forming methodologies that can otherwise be difficult to achieve with a metal reductant.
Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B 2 Pin 2 ) is described as a non‐metallic reductant in mediating Ni‐catalyzed C(sp 3 )–C(sp 2 ) reductive cross‐coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono‐functionalization of diols and bio‐relevant alcohols (e.g., carbohydrates). The use of B 2 Pin 2 shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross‐electrophile coupling chemistry that B 2 Pin 2 can sever as a reductant to reduce Ni II to Ni 0 . This mechanistic insight may inspire the development of new reductive bond‐forming methodologies that can otherwise be difficult to achieve with a metal reductant. The use of economic bis(pinacolato)diboron as the non‐metal reductant to direct the Ni‐catalyzed reductive arylation and vinylation of alkyl halides/ Katritzky salts with the C(sp 2 )–halides are achieved, which is characteristic of easy removal of boron residue and homogeneous nature of the reaction that are critical concerns for large‐scale and eco‐friendly process chemistry.
Abstract Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non‐metallic reductant in mediating Ni‐catalyzed C(sp3)–C(sp2) reductive cross‐coupling of alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides and alkyl halides/Katritzky salts. The present study is compatible with an in situ halogenation of alcohol method, allowing for selective mono‐functionalization of diols and bio‐relevant alcohols (e.g., carbohydrates). The use of B2Pin2 shows potential for easy scalability without introducing additional metal impurities into the products. It is observed for the first time in the realm of cross‐electrophile coupling chemistry that B2Pin2 can sever as a reductant to reduce NiII to Ni0. This mechanistic insight may inspire the development of new reductive bond‐forming methodologies that can otherwise be difficult to achieve with a metal reductant.
Author Gong, Hegui
Sun, Deli
Chen, Yunrong
Wu, Yu
Gong, Yuxin
AuthorAffiliation 2 Center for Supramolecular Chemistry and Catalysis Department of Chemistry Shanghai University Shanghai 200444 China
1 School of Resources and Environmental Engineering Shanghai Polytechnic University No. 2360 Jinhai Road Shanghai 201209 China
AuthorAffiliation_xml – name: 2 Center for Supramolecular Chemistry and Catalysis Department of Chemistry Shanghai University Shanghai 200444 China
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Issue 31
Keywords electrophile
nickel
diboron
cross‐coupling
reductant
Language English
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Snippet Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non‐metallic reductant in mediating Ni‐catalyzed...
Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B 2 Pin 2 ) is described as a non‐metallic reductant in mediating...
Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B Pin ) is described as a non-metallic reductant in mediating Ni-catalyzed...
Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non-metallic reductant in mediating Ni-catalyzed...
Abstract Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B2Pin2) is described as a non‐metallic reductant in mediating...
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StartPage e2404301
SubjectTerms Alcohol
cross‐coupling
diboron
electrophile
Hydrocarbons
Ligands
nickel
reductant
Solvents
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Title Bis(pinacolato)diboron‐Enabled Ni‐Catalyzed Reductive Arylation/Vinylation of Alkyl Electrophiles
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fadvs.202404301
https://www.ncbi.nlm.nih.gov/pubmed/38887210
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https://www.proquest.com/docview/3070794268
https://pubmed.ncbi.nlm.nih.gov/PMC11336967
https://doaj.org/article/82bdb6f8dc3848f483a5087c4cc57dc8
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