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Synlett 2022; 33(11): 1065-1070
DOI: 10.1055/a-1822-2832
letter

Cu/Mn-Catalyzed C–N Cross-Coupling Reaction of Aryl Chlorides and Amines Promoted by a Polyamidoamine Dendrimer

Archana Ranjan
a   Amity Institute of Microbial Technology, Amity University, Noida, 201313, Uttar Pradesh, India
,
Ajit Varma
a   Amity Institute of Microbial Technology, Amity University, Noida, 201313, Uttar Pradesh, India
,
Sangeeta Kumari
b   Department of Chemistry, Malaviya National Institute of Technology Jaipur, JLN Marg, Jaipur 302017, Rajasthan, India
,
Raj K. Joshi∗
b   Department of Chemistry, Malaviya National Institute of Technology Jaipur, JLN Marg, Jaipur 302017, Rajasthan, India
› Author AffiliationsR.K.J. thanks CSIR [01(2996)/19/EMR-II] for financial assistance.
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Abstract

A bimetallic catalytic combination of Mn(OAc)2 and Cu(OAc)2 was found to be significantly effective for the Buchwald-type C–N cross-coupling of aryl chlorides and amines. The reaction was markedly affected by the presence of a poly(amidoamine) dendrimer as a promoter that also possesses the advantages of being stable, nontoxic, biocompatible, nonimmunogenic, and acting as a soluble support for the transition-metal complex. Although, manganese is cheap and environmentally benign, it has not been fully exploited, due to its low intrinsic catalytic activity. Here, the catalytic potential of manganese was drastically increased by the presence of another metal salt, Cu(OAc)2. In the bimetallic composition, Mn significantly influenced the activity and selectivity, and played a vital role in catalysis. We have developed a novel, green, and economical procedure for Buchwald-type C–N cross-coupling of aryl chlorides and amines. This coupling method works under aerobic and solvent-free conditions and gives excellent yields of value-added N-arylated or N-alkylated products.

Key words

C–N coupling - manganese catalysis - copper catalysis - bimetal catalysis - dendrimers - Buchwald reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/ a-1822-2832.
  • Supporting Information


Publication History

Received: 07 February 2022

Accepted after revision: 11 April 2022

Accepted Manuscript online:
11 April 2022

Article published online:
24 May 2022

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