Hydrogenation of thiophens via the consecutive electron and proton transfer to thiophenium ions

Lyakhovetsky, Yury I.; Kalinkin, M. I.; Парнес, З. Н.; Latypova, F. M.; Kursanov, D. I.

doi:10.1039/c39800000766

Cited by 16 publications

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“…Apparently, FriedelÀCrafts reactions are not only difficult for phenols, but also for benzenethiols. We successfully synthesized 3a, instead, by the reduction of 2a with the Zn and TFA couple [12]. Similarly, 3b was synthesized by reduction of 2b with Zn and TFA (Scheme 1).…”

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confidence: 98%

Synthesis of 4,6‐Dimethyldibenzothiophene and 1,2,3,4‐Tetrahydro‐4,6‐dimethyldibenzothiophene via Tilak Annulation

Wang

et al. 2011

Helvetica Chimica Acta

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1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohexanone with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. A mixture of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene and 4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohex-2-en-1-one with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. 2-Bromo-3-methylcyclohexanone was synthesized by conjugate addition of Me 3 Al to 2-bromocyclohex-2-en-1-one with CuBr as catalyst and 2-bromo-3-methylcyclohex-2-en-1-one by brominationÀelimination of 3-methylcyclohex-2-en-1-one. 1,2,3,4,4a,9b-Hexahydro-4,6-dimethyldibenzothiophene was prepared by reduction of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene with Zn and CF 3 COOH.

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Synthesis of 4,6‐Dimethyldibenzothiophene and 1,2,3,4‐Tetrahydro‐4,6‐dimethyldibenzothiophene via Tilak Annulation

Wang

et al. 2011

Helvetica Chimica Acta

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“…We successfully synthesized 4,6-DM-HHDBT instead by the reduction of 4,6-DM-THDBT with the Zn-trifluoroacetic acid couple. 13 Alternatively, 4,6-DM-THDBT can be hydrogenated by transfer hydrogenation with a secondary alcohol, as in the dehydrogenation of secondary alcohols with styrene over a Cu catalyst. 14 4,6-DM-THDBT can be easily dehydrogenated to 4,6-DMDBT by reaction with sulfur, selenium or a Pd catalyst, or by transfer dehydrogenation (Scheme 2).…”

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Synthesis of 4,6-dimethyl-tetrahydro- and hexahydro-dibenzothiophene

Sun

Wang

Prins

2008

Tetrahedron Letters

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“…The reduction of thiophenes to 2,5-dihydrothiophenes has also been reported (eq. 3) (46). It was hoped that such a transformation, followed by selective desulfurization CK + Zn/CFgCOgH CH.Cl.…”

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Organopalladium approaches to bicyclic heteraotom containing prostaglandin analogues

LEACH

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CHAPTER I. INTRODUCTION 1 CHAPTER II. SYNTHESIS OF HETEROCYCLIC PROSTAGLANDIN ENDOPEROXIDE ANALOGOUS 13 Conclusion 55 Experimental 56 CHAPTER III. SYNTHESIS OF 7-OXA PROSTAGLANDIN ENDOPEROXIDE ANALOGUES 79 Conclusion 100 Experimental 101 CHAPTER IV. ORGANOCOPPER-ORGANOMERCURY CROSS-COUPLING REACTIONS 116 The following chapter describes the results of work directed towards the synthesis of thiophene containing prostaglandin analogues. Chapter III describes the synthesis of several 7-oxa prostaglandin analogues. Chapter IV gives the results of the exploration of a new reaction for the alkylation of organomercurials with organocuprates, a reaction we hoped would be useful in several prostaglandin syntheses. Lastly, Chapter V briefly summarizes the results of this research and presents some suggestions for future work.

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Hydrogenation of thiophens via the consecutive electron and proton transfer to thiophenium ions

Cited by 16 publications

References 0 publications

Synthesis of 4,6‐Dimethyldibenzothiophene and 1,2,3,4‐Tetrahydro‐4,6‐dimethyldibenzothiophene via Tilak Annulation

Synthesis of 4,6‐Dimethyldibenzothiophene and 1,2,3,4‐Tetrahydro‐4,6‐dimethyldibenzothiophene via Tilak Annulation

Synthesis of 4,6-dimethyl-tetrahydro- and hexahydro-dibenzothiophene

Organopalladium approaches to bicyclic heteraotom containing prostaglandin analogues

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