One‐Step Synthesis of Acylboron Compounds via Copper‐Catalyzed Carbonylative Borylation of Alkyl Halides

A copper‐catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of function...

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Published inAngewandte Chemie International Edition Vol. 60; no. 4; pp. 2094 - 2098
Main Authors Cheng, Li‐Jie, Zhao, Siling, Mankad, Neal P.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 25.01.2021
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
acylboron
B2pin2
carbonylative borylation
Carbonyls
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Copper
Copper compounds
Functional groups
Halides
Intermediates
KATs
Physical Sciences
Potassium
Science & Technology
CONVENIENT SYNTHESIS
TRIALKYLBORANES
BORON
Bpin
carbonylative borylation
CARBON MONOXIDE
ORGANOBORANES
KATs
acylboron
ACYLTRIFLUOROBORATE
copper
ATMOSPHERIC PRESSURE
RADICALS
DIBORATION
CYCLIZATION
B2pin2
Online AccessGet full text
ISSN1433-7851
1521-3773
1521-3773
DOI10.1002/anie.202012373

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Abstract A copper‐catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N‐methyliminodiacetyl (MIDA) acylboronates as well as α‐methylated potassium acyltrifluoroborates in a one‐pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin. A copper‐catalyzed carbonylative borylation of unactivated alkyl halides enables one‐step synthesis of acylborons which can be further transformed into potassium acyltrifluoroborates (KATs) as well as N‐methyliminodiacetyl (MIDA) acylboronate in a one‐pot manner.
AbstractList A copper‐catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF 2 . A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N ‐methyliminodiacetyl (MIDA) acylboronates as well as α‐methylated potassium acyltrifluoroborates in a one‐pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.
A copper‐catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N‐methyliminodiacetyl (MIDA) acylboronates as well as α‐methylated potassium acyltrifluoroborates in a one‐pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.
A copper-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF . A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.
A copper‐catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N‐methyliminodiacetyl (MIDA) acylboronates as well as α‐methylated potassium acyltrifluoroborates in a one‐pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin. A copper‐catalyzed carbonylative borylation of unactivated alkyl halides enables one‐step synthesis of acylborons which can be further transformed into potassium acyltrifluoroborates (KATs) as well as N‐methyliminodiacetyl (MIDA) acylboronate in a one‐pot manner.
A copper-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as alpha-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.
A copper-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2 . A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.A copper-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2 . A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.
Author Zhao, Siling
Mankad, Neal P.
Cheng, Li‐Jie
Author_xml – sequence: 1
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  fullname: Cheng, Li‐Jie
  organization: University of Illinois at Chicago
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  givenname: Siling
  surname: Zhao
  fullname: Zhao, Siling
  organization: University of Illinois at Chicago
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  surname: Mankad
  fullname: Mankad, Neal P.
  email: npm@uic.edu
  organization: University of Illinois at Chicago
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Issue 4
Keywords CONVENIENT SYNTHESIS
TRIALKYLBORANES
BORON
Bpin
carbonylative borylation
CARBON MONOXIDE
ORGANOBORANES
KATs
acylboron
ACYLTRIFLUOROBORATE
copper
ATMOSPHERIC PRESSURE
RADICALS
DIBORATION
CYCLIZATION
B2pin2
Language English
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Notes https://doi.org/10.26434/chemrxiv.12818180.v1
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A previous version of this manuscript has been deposited on a preprint server
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Snippet A copper‐catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium...
A copper-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium...
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SubjectTerms acylboron
B2pin2
carbonylative borylation
Carbonyls
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Copper
Copper compounds
Functional groups
Halides
Intermediates
KATs
Physical Sciences
Potassium
Science & Technology
Title One‐Step Synthesis of Acylboron Compounds via Copper‐Catalyzed Carbonylative Borylation of Alkyl Halides
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202012373
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https://www.ncbi.nlm.nih.gov/pubmed/33090619
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https://www.proquest.com/docview/2453689135
Volume 60
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