Synthesis of β,β-Dithioketones by Merging C–C and C–S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation

An unconventional [1 + 1 + 1 + 1 + 1 + 1] annulation process was developed for the construction of β,β-dithioketones by merging C–C and C–S bond cleavage. In this reaction, rongalite concurrently served as triple C1 units, dual sulfur­(II) synthons, and a reductant for the first time. Mechanism inve...

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Published inOrganic letters Vol. 26; no. 20; pp. 4340 - 4345
Main Authors Yang, Dong-Sheng, Chen, Xiang-Long, Wu, Chun-Yan, Tang, Bo-Cheng, Xiao, Yong-Cheng, Wu, Yan-Dong, Wu, An-Xin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.05.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACYL ANION EQUIVALENTS
1,3-DITHIANES
INSERTION
DITHIANES
SULFUR-DIOXIDE
RONGALITE
CATALYZED REGIOSELECTIVE SULFENYLATION
CARBANIONS
INDOLES
CONJUGATE ADDITION
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Summary:An unconventional [1 + 1 + 1 + 1 + 1 + 1] annulation process was developed for the construction of β,β-dithioketones by merging C–C and C–S bond cleavage. In this reaction, rongalite concurrently served as triple C1 units, dual sulfur­(II) synthons, and a reductant for the first time. Mechanism investigation indicated that the reaction involved the self-mediated valence state change of rongalite. By performing this step-economical method, the challenging construction of C5-substituted 1,3-dithiane can be achieved under mild and simple conditions.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c01364