ChemInform Abstract: Iodine‐Catalyzed Selective Synthesis of 2‐Sulfanylphenols via Oxidative Aromatization of Cyclohexanones and Disulfides.

Ge, Wenlei; Zhu, Xun; Wei, Yunyang

doi:10.1002/chin.201415093

Cited by 2 publications

(3 citation statements)

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“…The starting sulfide 2-[(4-methylphenyl)thio]-2-cyclopenten-1-one 2 was synthesized according to known procedures [28,29]. In our hands the best yield of sulfide 2 was only 38%, although the published yields are around 65%.…”

Section: Synthesis Of Enantioenriched 2-(s)-[(4-methylphenyl) Sulfiny...mentioning

confidence: 82%

Synthesis of 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one, a D-ring precursor of 9,11-secosterols

Kõllo¹,

Rõuk²,

Lopp³

2022

PEAS

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The asymmetric oxidation of a key intermediate for 9,11-secosterol synthesis, 2-[(4-methylphenyl)thio]-2-cyclopenten-1one 2 with a Ti(iPrO) 4 /(+)-DET/TBHP complex was studied. The kinetic resolution of racemic 2-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one 1 by oxidation with the same Ti-complex was also carried out. In both cases enantioenriched 2-(S)-[(4methylphenyl)sulfinyl]-2-cyclopenten-1-one 1 was obtained in satisfactory yields and sufficient enantiomeric purity for further enantioenrichment by recrystallization. The obtained results afford simple access to the D-ring precursor of 9,11-secosterols.

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Section: Synthesis Of Enantioenriched 2-(s)-[(4-methylphenyl) Sulfiny...mentioning

confidence: 82%

Synthesis of 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one, a D-ring precursor of 9,11-secosterols

Kõllo¹,

Rõuk²,

Lopp³

2022

PEAS

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“…In 2013, Wei et al . described an iodine‐catalyzed aerobic dehydrogenative aromatization of cyclohexanones and disulfides for the synthesis of 2‐sulfanylphenols . With the development of transition metal‐catalyzed C─hydrogen (H) activation, direct C─H hydroxylation was regarded as one of the efficient avenues for the introduction of the desired functional group on the selected targets .…”

Section: Introductionmentioning

confidence: 99%

“…[14][15][16] In 2013, Wei et al described an iodine-catalyzed aerobic dehydrogenative aromatization of cyclohexanones and disulfides for the synthesis of 2-sulfanylphenols. 17 With the development of transition metal-catalyzed C─hydrogen (H) activation, direct C─H hydroxylation was regarded as one of the efficient avenues for the introduction of the desired functional group on the selected targets. [18][19][20][21][22][23][24][25][26][27][28][29] Therefore, it was considered as a novel strategy to obtain functionalized phenols based on the hydroxylation of inert C─H bonds.…”

Section: Introductionmentioning

confidence: 99%

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

Zhang

Wang

et al. 2020

J of Chemical Tech & Biotech

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BACKGROUND Aromatic thioether derivatives exist widely in natural products and have significant applications in modern synthesis and the pharmaceutical industry; for example, 2‐sulfanylphenols and arylthioquinones are important intermediates in the processing of anticancer, antibiotic, antivirus and antimalarial drugs. Direct C─H hydroxylation was considered as one of the efficient methods for the synthesis of these compounds. Homogeneous transition metal catalysts usually were used through a cross‐coupling of halogen‐substituted phenols with thiophenols. However, from the perspectives of sustainable development and easy recovery, it is necessary to develop an efficient and recoverable catalytic system to realize the synthesis of aromatic thioether derivatives with good efficiency and recyclability. RESULTS The heterogeneous catalyst [Cu(binap)I]2@HT in the present work showed good catalytic activity for the C─H hydroxylation of benzenethiol and phenylboronic acid. The catalytic system was tolerant to various substituents including alkyl, alkoxy, ester, halogen or trifluoromethyl on the phenyl ring of the thiophenols or arylboric acids. In addition to electron‐donating groups, the products with strong electron‐withdrawing groups, such as methyl formylate and trifluoromethyl also were achieved with good yields at 90 °C for 12 h (68% and 66%, respectively). Repeated experiment results showed that the catalyst could be reused at least five times without obvious decrease in catalytic activity. CONCLUSION A BINAP‐Cu complex supported on hydrotalcite was prepared and used as a heterogeneous catalyst for the C─H activation of thiophenol under mild reaction conditions. Through a cascade C─H hydroxylation and further oxidation process, 2‐Sulfanylphenols and arylthioquinones could be obtained with moderate‐to‐good yields for a series of 2‐(phenylthio)phenol derivatives using the heterogeneous catalyst [Cu(binap)I]2@HT. In addition, this heterogeneous catalyst showed good recylbility. © 2020 Society of Chemical Industry

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ChemInform Abstract: Iodine‐Catalyzed Selective Synthesis of 2‐Sulfanylphenols via Oxidative Aromatization of Cyclohexanones and Disulfides.

Cited by 2 publications

References 1 publication

Synthesis of 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one, a D-ring precursor of 9,11-secosterols

Synthesis of 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one, a D-ring precursor of 9,11-secosterols

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

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