Selective N‐Monovinylation of Primary Aromatic Amides Using Calcium Carbide as an Alkyne Source

Abstract

An efficient method for the selective N‐monovinylation of primary aromatic amides using calcium carbide as an alkyne source is described. A series of N‐vinylbenzamides (enamides) were readily synthesized by this strategy. The salient features for this protocol are the use of inexpensive, easy‐to‐handle solid alkyne source, high chemoselectivity, transition metal catalyst‐free, good functional group tolerance, and simple work‐up procedures. These reactions can also be extended to the gram‐scale level.

A 60-times faster digital-discovery-compatible reaction setup with enhanced safety for chemical applications

“…ditions, bypassing the need for autoclaves. [105][106][107][108][109] The yield of benzyl vinyl ether was consistent, irrespective of the presence or absence of PLA (Scheme 2D).…”

Sustainable application of calcium carbide residue as a filler for 3D printing materials

“…Manufacturing acetylene from calcium carbide is the current hydrocarbon-free method of industrial acetylene production. Moreover, calcium carbide has some advanced applications in organic synthesis [22][23][24][25][26][27][28][29][30] , catalysis [31][32][33][34] , mechanosynthesis 31,35 and materials science 36 , with a continuous increase in interest in acetylene-based technologies due to the efficiency of atom-economic addition reactions. However, acetylene release is accompanied by the formation of calcium carbide residue (CCR), which is simply disposed and accumulates in landfills 37,38 .…”

Atom-economical synthesis of 1,2-bis(phosphine oxide)ethanes from calcium carbide with straightforward access to deuterium- and13C-labeled bidentate phosphorus ligands and metal complexes

“…1D). The chemistry of calcium carbide is a well-developed area 98,99 with a number of representative studies, 100–113 including triple bond transformations under superbasic conditions. 114–121…”

“…1D). The chemistry of calcium carbide is a well-developed area 98,99 with a number of representative studies, [100][101][102][103][104][105][106][107][108][109][110][111][112][113] including triple bond transformations under superbasic conditions. [114][115][116][117][118][119][120][121] Here, we extend the synthetic methodology to develop costefficient and convenient isotopic labeling.…”