Skip to main content

Lund University Publications

LUND UNIVERSITY LIBRARIES

Highly Efficient Base Catalyzed N-alkylation of Amines with Alcohols and β-Alkylation of Secondary Alcohols with Primary Alcohols

Garg, Nitish K. LU ; Tan, Mattias LU ; Johnson, Magnus T. LU and Wendt, Ola F. LU (2023) In ChemCatChem 15(20).
Abstract

Borrowing hydrogen (BH) reactions are very useful for the sustainable synthesis of C−C and C−N bonds. They generally operate with transition metal-based catalysts along with stoichiometric/catalytic amounts of added base. Here we report that two catalytic transformations, generally carried out with the BH methodology, i. e. N-alkylation of amines with alcohols and β-alkylation of secondary alcohols with primary alcohols, can be performed very effectively with just catalytic amounts of base under air without using any transition metal-based catalyst. The mechanism is proposed to be based on air oxidation of the alcohol to aldehyde followed by condensation to an unsaturated intermediate which undergoes transfer hydrogenation with alcohol... (More)

Borrowing hydrogen (BH) reactions are very useful for the sustainable synthesis of C−C and C−N bonds. They generally operate with transition metal-based catalysts along with stoichiometric/catalytic amounts of added base. Here we report that two catalytic transformations, generally carried out with the BH methodology, i. e. N-alkylation of amines with alcohols and β-alkylation of secondary alcohols with primary alcohols, can be performed very effectively with just catalytic amounts of base under air without using any transition metal-based catalyst. The mechanism is proposed to be based on air oxidation of the alcohol to aldehyde followed by condensation to an unsaturated intermediate which undergoes transfer hydrogenation with alcohol to the product.

(Less)
Please use this url to cite or link to this publication:
author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Amination, Borrowing hydrogen, C-alkylation, Catalysis, Transition metal-free
in
ChemCatChem
volume
15
issue
20
article number
e202300741
publisher
John Wiley & Sons Inc.
external identifiers
  • scopus:85168612405
ISSN
1867-3880
DOI
10.1002/cctc.202300741
language
English
LU publication?
yes
id
9c574adb-b8a6-426a-9cb9-7342630bc133
date added to LUP
2023-11-10 12:58:06
date last changed
2023-11-10 12:59:21
@article{9c574adb-b8a6-426a-9cb9-7342630bc133,
  abstract     = {{<p>Borrowing hydrogen (BH) reactions are very useful for the sustainable synthesis of C−C and C−N bonds. They generally operate with transition metal-based catalysts along with stoichiometric/catalytic amounts of added base. Here we report that two catalytic transformations, generally carried out with the BH methodology, i. e. N-alkylation of amines with alcohols and β-alkylation of secondary alcohols with primary alcohols, can be performed very effectively with just catalytic amounts of base under air without using any transition metal-based catalyst. The mechanism is proposed to be based on air oxidation of the alcohol to aldehyde followed by condensation to an unsaturated intermediate which undergoes transfer hydrogenation with alcohol to the product.</p>}},
  author       = {{Garg, Nitish K. and Tan, Mattias and Johnson, Magnus T. and Wendt, Ola F.}},
  issn         = {{1867-3880}},
  keywords     = {{Amination; Borrowing hydrogen; C-alkylation; Catalysis; Transition metal-free}},
  language     = {{eng}},
  number       = {{20}},
  publisher    = {{John Wiley & Sons Inc.}},
  series       = {{ChemCatChem}},
  title        = {{Highly Efficient Base Catalyzed N-alkylation of Amines with Alcohols and β-Alkylation of Secondary Alcohols with Primary Alcohols}},
  url          = {{http://dx.doi.org/10.1002/cctc.202300741}},
  doi          = {{10.1002/cctc.202300741}},
  volume       = {{15}},
  year         = {{2023}},
}