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			<titleStmt><title level='a'>Synthesis of iodonium ylides stabilized by internal halogen bonding</title></titleStmt>
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				<publisher>American Chemical Society</publisher>
				<date>03/23/2025</date>
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					<idno type="par_id">10586082</idno>
					<idno type="doi"></idno>
					<title level='j'>Abstracts of papers  American Chemical Society</title>
<idno>0065-7727</idno>
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					<author>N Zarrabi</author><author>V Zhdankin</author><author>S Krystosek</author><author>G Hughes</author>
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			<abstract><ab><![CDATA[Iodonium ylides are important carbene precursors with many synthetic applications. 1,2 Most of the known iodonium ylides have low thermal stability and slowly decompose at room temperature, which restricts their practical application. We report the preparation of new iodonium ylides in which hypervalent iodine center is coordinated by halogen bonding with a halogen (Cl or Br) in the orthoposition of aromatic ring. Additional coordination of the hypervalent center results in significant stabilization of the ylide.The ortho-substituted malonate ylides 3 were synthesized in moderate yields starting from commercially available aryl iodides 1 by peracetic acid oxidation to (diacetoxyiodo)arenes 2 followed by reaction with ethyl or methyl malonate esters under basic conditions. Ylides 3 were isolated as thermally stable, microcrystalline solids with melting points between 105-134 o C. All new compounds were characterized using NMR spectroscopy and high-resolution mass spectrometry.]]></ab></abstract>
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<div xmlns="http://www.tei-c.org/ns/1.0"><p>The newly synthesized iodonium ylides are potentially useful reagents as carbene precursors in C-H insertion reactions, cyclopropanation of alkenes, and as reagents for transylidation.</p><p>1. Yusubov, M. S.; Yoshimura, A.; Zhdankin, V. V. Iodonium Ylides in Organic Synthesis. Arkivoc. 2016, 1, 342-374. 2. Yoshimura, A.; Zhdankin, V. V. Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents. Chem. Rev. 2024, 124, ASAP.</p><p>Me or Et) OR RO O O 50-60%</p></div>		</body>
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