Abstract: Constructing molecular complexity from simple precursors stands as a cornerstone in contemporary organic synthesis. Systems harnessing easily accessible starting materials, which offer control over stereochemistry and support a modular assembly approach, are particularly in demand. In this research, we utilized calcium carbide, presenting a sustainable pathway to generate acetylene gas – a fundamental C2 building block. We performed a Pt-facilitated linkage of two C2-units sourced from two calcium carbide molecules to craft a conjugated C4 core with exceptional stereoselectivity. As a benchmark, we selected the synthesis of (E,E)-1,4-diiodobuta-1,3-diene, executing it in a two-chamber reactor. Compartmentalization of the reactions across these chambers resulted in the desired product in 85% yield. Furthermore, high-energy polymeric substances were derived by marrying the molecular intricacy between (E,E)-1,4-diiodobuta-1,3-diene and calcium carbide, underpinning a unique C4+C2 assembly blueprint. The structure and morphology of the polymeric material were characterized by IR and NMR spectroscopy, scanning electron microscopy, and energy dispersive X-ray spectroscopy. Overall, two complementary 2×C2-to-C4 and (2×C2+C’2)×n assembly schemes were developed using Pt and Pd catalysis.

Cite: Potorochenko A.N. , Rodygin K.S. , Ananikov V.P.
Assembly of (2×C2+C’2)×n Molecular Complexity Using a Sequence of Pt‐ and Pd‐Catalyzed Transformations with Calcium Carbide
European Journal of Organic Chemistry. 2024. V.27. N4. e202301012 . DOI: 10.1002/ejoc.202301012 WOS Scopus OpenAlex

Identifiers:

Web of science:	WOS:001128641300001
Scopus:	2-s2.0-85180232168
OpenAlex:	W4389078104

Citing:

DB	Citing
OpenAlex	2
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