Abstract
The development of new drugs is accelerated by rapid access to functionalized and D-labeled molecules with improved activity and pharmacokinetic profiles. Diverse synthetic procedures often involve the usage of gaseous reagents, which can be a difficult task due to the requirement of a dedicated laboratory setup. Here, we developed a special reactor for the on-demand production of gases actively utilized in organic synthesis (C2H2, H2, C2D2, D2, and CO2) that completely eliminates the need for high-pressure equipment and allows for integrating gas generation into advanced laboratory practice. The reactor was developed by computer-aided design and manufactured using a conventional 3D printer with polypropylene and nylon filled with carbon fibers as materials. The implementation of the reactor was demonstrated in representative reactions with acetylene, such as atom-economic nucleophilic addition (conversions of 19–99%) and nickel-catalyzed S-functionalization (yields 74–99%). One of the most important advantages of the reactor is the ability to generate deuterated acetylene (C2D2) and deuterium gas (D2), which was used for highly significant, atom-economic and cost-efficient deuterium labeling of S,O-vinyl derivatives (yield 68–94%). Successful examples of their use in organic synthesis are provided to synthesize building blocks of heteroatom-functionalized and D-labeled biologically active organic molecules.
Highlights
The development of new drugs urgently requires accelerated chemical synthesis procedures to access key molecular building blocks and synthesize libraries of new molecules.Modular synthetic procedures based on simple starting materials are demanded the most to achieve cost-efficient and rapid preparation of new organic molecules
We found that the design of the reactor for acetylene generation using 3D printing technology provides a complete solution to this complex problem
For the reactor to be compact, it should fit into a reaction vessel. This reactor should have a minimum of joints, which reduces the risk of possible uncontrolled and significant leaks and the loss of generated acetylene
Summary
The development of new drugs urgently requires accelerated chemical synthesis procedures to access key molecular building blocks and synthesize libraries of new molecules. Modular synthetic procedures based on simple starting materials are demanded the most to achieve cost-efficient and rapid preparation of new organic molecules. The use of acetylenic starting materials is one of the most efficient ways to achieve cost-efficient functionalization in eco-friendly organic synthesis with reduced generation of wastes. Acetylene is one of the most important building blocks in organic synthesis due to its availability and the many transformations developed, such as vinylation [1], carbonylation [2,3], Favorsky reactions [4], and coupling reactions [5], among many others [6,7,8]. The transformations of acetylene have been implemented in industrial processes [10] and used in the development of a new generation of smart multifunctional materials [11,12]
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