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Synfacts 2020; 16(12): 1459
DOI: 10.1055/s-0040-1706559
Polymer-Supported Synthesis

Decarboxylative Alkynylation of Carboxylic Acid Promoted by Graphitic Carbon Nitride

Contributor(s):
Yasuhiro Uozumi
,
Shintaro Okumura
Guo J, Wang Y, Li Y, Lu K, Liu S, Wang W, *, Zhang Y. * East China University of Science and Technology, Shanghai, P. R. of China and University of Arizona, Tucson, USA
Graphitic Carbon Nitride Polymer as a Recyclable Photoredox Catalyst for Decarboxylative Alkynylation of Carboxylic Acids.

Adv. Synth. Catal. 2020;
362: 3898-3904
DOI: 10.1002/adsc.202000777
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Key words

carboxylic acids - graphitic carbon nitride - photoredox catalysis - alkynylation - decarboxylation

Significance

Graphitic carbon nitride (g-C3N4) promoted the decarboxylative alkynylation of carboxylic acids 1 with 1-alkynyl-1λ3,2-benziodoxol-3(1H)-ones 2 to give the corresponding alkynes 3 in ≤97% yield (eq. 1). g-C3N4 also promoted the 1,2-amidoalkynylation of alkenes 5 with Troc-protected amino oxy acid 4 and phenyl-EBX (6) to give the corresponding alkynes 7 in ≤80% yield (eq. 2).


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Comment

In the decarboxylative alkynylation of N-Boc-proline with 6, the catalyst was recovered and reused seven times without significant loss of its catalytic activity. Large-scale reactions could be performed in a continuous-flow fashion. A 6.6 mmol scale reaction of N-Boc-proline with 6 gave 1.3 g of the alkynylated product.


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Publication History

Article published online:
17 November 2020

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