Assembly of (2×C2+C’2)×n Molecular Complexity Using a Sequence of Pt‐ and Pd‐Catalyzed Transformations with Calcium Carbide

Author:

Potorochenko Anton N.1ORCID,Rodygin Konstantin S.1ORCID,Ananikov Valentine P.12ORCID

Affiliation:

1. Institute of Chemistry Saint Petersburg State University 7/9 Universitetskaya nab. 199034 St. Petersburg Russia

2. N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Leninsky pr. 47 119991 Moscow Russia

Abstract

AbstractConstructing 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.

Funder

Saint Petersburg State University

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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