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Divergent Halogenation Pathways of 2,2‐Dichlorobut‐3‐yn‐1‐ols to 3‐Chloro‐4‐Iodofurans and α‐Chloro‐γ‐Iodoallenes: Electrophilic versus Pd(II)‐Catalyzed Halogenation Strategies
Author(s) -
Abozeid Mohamed Ahmed,
Kim Hun Young,
Oh Kyungsoo
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001033
Subject(s) - halogenation , chemistry , electrophile , halogen , catalysis , furan , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
Divergent halogenation pathways of 2,2‐dichlorobut‐3‐yn‐1‐ols have been developed to give 3,4‐dihalofurans and 1,3‐dihaloallenyl ketones in good to excellent yields. Thus, the readily accessible 2,2‐dichlorobut‐3‐yn‐1‐ols were treated with the electrophilic halogen source to provide the 1,3‐dihalogen‐substituted allenyl ketones, whereas the use of Pd(II) catalyst promoted the oxypalladation followed by the electrophilic halogenation to give 3,4‐dihalogen‐substituted furan derivatives. The synthetic utility of 3,4‐dihalofurans and 1,3‐dihaloallenyl ketones is demonstrated in the sequential Suzuki cross coupling strategies.