Manganese(I)-Catalyzed Direct Addition of C(sp<sup>3</sup>)–H Bonds to Aryl Isocyanates

The addition of C-H bonds to isocyanates catalyzed by transition metals is a highly auspicious methodology for providing synthetically and biologically important amides. However, the substrates are limited to C(sp<sup>2</sup>)-H bonds. In this work, an efficient manganese(I)-catalyzed direct addition reaction of C(sp<sup>3</sup>)-H bonds of 8-methylquinolines to aryl isocyanates has been developed, leading to the synthesis of various α-quinolinyl amide compounds in moderate to high yields. The reaction has a broad range of substrates and a good functional group tolerance. A possible mechanism is proposed based on the experimental results.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-03
DOI
https://doi.org/10.1021/acs.joc.4c01581
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.50

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article

Manganese(I)-Catalyzed Direct Addition of C(sp3)–H Bonds to Aryl Isocyanates

Baiquan Wang, Zhichao Yu, Bin Li, Hongxin Liu
2 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.50
article

Manganese(I)-Catalyzed Direct Addition of C(sp3)–H Bonds to Aryl Isocyanates

Baiquan Wang, Zhichao Yu, Bin Li, Hongxin Liu
article en
2 citations

Abstract

The addition of C-H bonds to isocyanates catalyzed by transition metals is a highly auspicious methodology for providing synthetically and biologically important amides. However, the substrates are limited to C(sp<sup>2</sup>)-H bonds. In this work, an efficient manganese(I)-catalyzed direct addition reaction of C(sp<sup>3</sup>)-H bonds of 8-methylquinolines to aryl isocyanates has been developed, leading to the synthesis of various α-quinolinyl amide compounds in moderate to high yields. The reaction has a broad range of substrates and a good functional group tolerance. A possible mechanism is proposed based on the experimental results.

The Journal of Organic ChemistryVol. 89(18)
Chinese Academy of Sciences (CN), Nankai University (CN), Shanghai Institute of Organic Chemistry (CN)
National Natural Science Foundation of China, Natural Science Foundation of Tianjin City
Clean water and sanitation
Openalex Percentile: Top 40%
Catalytic C–H Functionalization Methods
0.50
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