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Reactions of thiocarbonyl compounds with electrophilic and nucleophilic carbenes as well as with their metal complexes

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Pages 672-700 | Received 29 Apr 2020, Accepted 04 Jun 2020, Published online: 02 Jul 2020

References

  • Huisgen R, Li X, Giera H, et al. ‘Thiobenzophenone S-methylide’ (= (diphenylmethylidenesulfonio)methanide), and C,C multiple bonds: cycloadditions and dipolarophilic reactivities. Helv Chim Acta. 2001;84:981–999. doi: 10.1002/1522-2675(20010516)84:5<981::AID-HLCA981>3.0.CO;2-O
  • Huisgen R, Fisera L, Giera H, et al. Thiones as superdipolarophiles. Rates and equilibria of nitrone cycloaddiitons to thioketones. J Am Chem. Soc. 1995;117:9671–9678. doi: 10.1021/ja00143a008
  • Huisgen R, Langhals E. 1,3-Dipolar cycloadditions of diphenyldiazomethane to thiones: rate measurements disclose thiones to be superdipolarophiles. Heteroatom Chem. 2006;17:433–442. doi: 10.1002/hc.20262
  • Rohr U, Schatz J, Sauer J. Thio- and selenocarbonyl compounds as ‘superdienophiles’ in [4 + 2] cycloadditions. Eur J Org Chem. 1998: 2875–2883. doi: 10.1002/(SICI)1099-0690(199812)1998:12<2875::AID-EJOC2875>3.0.CO;2-N
  • Staudinger H, Siegwart J. Einwirkungen von aliphatischen Diazoverbindungen auf thioketone. Helv Chim Acta. 1920;3:833–840. doi: 10.1002/hlca.19200030178
  • Schönberg A, Cernik D, Urban W. Über schwefelhaltige Analoga des Hexaphenyl-äthans, II. Ber Dtsch Chem Ges. 1931;64B:2577–2581. doi: 10.1002/cber.19310640941
  • Huisgen R, Fulka C, Kalwinsch I, et al. Recent developments of the chemistry of thiocarbonyl ylides. Bull Soc Chim Belg. 1984;93:511–532. doi: 10.1002/bscb.19840930701
  • Mlostoń G, Heimgartner H. Generation and typical reactions of thiocarbonyl ylides. Pol J Chem. 2000;74:1503–1532.
  • Mlostoń G, Heimgartner H. Thiocarbonyl ylides. In: Padwa A, Pearson WH, editors. 1,3-Dipolar cycloaddition chemistry towards heterocycles and natural products. New York (NY): Wiley; 2002. Chapter 5: p. 315–360.
  • Mlostoń G, Heimgartner H. Synthesis of five-membered sulfur-heterocycles via 1,5-dipolar electrocyclization of thiocarbonyl ylides and related processes. Curr Org Chem. 2011;15:675–693. doi: 10.2174/138527211794518961
  • Huisgen R, Binsch G, König H. Umsetzungen aromatischer Ketocarbene mit Heteromehrfachbindungen. Chem Ber. 1964;97:2868–2883. doi: 10.1002/cber.19640971018
  • Ibata T, Nakano H. Formation of 2-imino-1,3-oxathioles and 2(3H)-oxazolethione by rhodium(II) acetate-catalyzed reaction of α-diazocarbonyl compounds with isothiocyanates. Bull Chem Soc Jpn. 1992;65:3088–3093. doi: 10.1246/bcsj.65.3088
  • He X, Zhou Y, Shang Y, et al. Synthesis of 2-arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh2(OAc)4-catalyzed reactions of cyclic 2-diazo-1,3-diketones with aryl isothiocyanates. ACS Omega. 2016;1:1277–1283. doi: 10.1021/acsomega.6b00295
  • Nakano H, Ibata T. The rhodium(II)acetate-catalyzed reaction of alkenyl and alkynyl α-diazoacetates with thioketene. Bull Chem Soc Jpn. 1995;68:1393–1400. doi: 10.1246/bcsj.68.1393
  • Kelmendi B, Mlostoń G, Heimgartner H. Reactions of α-diazocycloalkanones with thiocarbonyl compounds. Heterocycles. 2000;52:475–482. doi: 10.3987/COM-99-S35
  • Kägi M, Linden A, Mlostoń G, et al. 1,3-Oxathiole and thiirane derivatives from the reaction of azibenzil and α-diazoamides with thiocarbonyl compounds. Helv Chim Acta. 1998;81:285–302. doi: 10.1002/hlca.19980810209
  • Mlostoń G, Pipiak P, Linden A, et al. 1,3-Dipolar cycloadditions of α-diazo ketones derived from N-protected (S)-proline with aromatic and cycloaliphatic thioketones. Helv Chim Acta. 2015;98:190–200. doi: 10.1002/hlca.201400334
  • Pipiak P, Mlostoń G. Selected applications of N-protected (S)-2-(diazoacetyl)pyrrolidines. Chem Heterocycl Compd. 2016;52:146–148. doi: 10.1007/s10593-016-1848-0
  • Mlostoń G, Hamera-Fałdyga R, Jeske M, et al. Microwave-assisted reactions of α-diazoketones with hetaryl and ferrocenyl thioketones. J Sulfur Chem. 2018;39:47–63. doi: 10.1080/17415993.2017.1363206
  • Mlostoń G, Urbaniak K, Szychowska A, et al. Thermal [2 + 2]-cycloadditions of diphenylketene with aryl- and hetaryl-substituted thioketones. Heterocycles. 2015;90:529–539. doi: 10.3987/COM-14-S(K)56
  • Nikolaev VA, Ivanov AV, Rodina LL, et al. Less reactive dipoles of diazodicarbonyl compounds in reaction with cycloaliphatic thioketones – first evidence for the 1,3-oxathiole–thiocarbonyl ylide interconversion. Beilstein J Org Chem. 2013;9:2751–2761. doi: 10.3762/bjoc.9.309
  • Nikolaev VA, Ivanov AV, Shakhmin AA, et al. The first examples of cycloadditions of 2-diazo-1,3-dicarbonyl compounds to aromatic thioketones. Tetrahedron Lett. 2012;53:3095–3099. doi: 10.1016/j.tetlet.2012.04.036
  • Mlostoń G, Grzelak P, Hamera-Fałdyga R, et al. Aryl, hetaryl, and ferrocenyl thioketones as versatile building blocks for exploration in the organic chemistry of sulfur. Phosphorus Sulfur Silicon Relat Elem. 2017;192:204–211. doi: 10.1080/10426507.2016.1252368
  • Kaepplinger C, Beckert R, Braunerova G, et al. Barton-Kellogg olefination of conjugated dithioxo compounds. Sulfur Lett. 2003;26:141–147. doi: 10.1080/02786110310001612263
  • Mlostoń G, Romański J, Heimgartner H. Reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone with dimethyl diazomalonate catalyzed by Rh2(OAc)4. J Pol Chem. 2002;76:551–555.
  • Koduri ND, Scott H, Hileman B, et al. Ruthenium catalyzed synthesis of enaminones. Org Lett. 2012;14:440–443. doi: 10.1021/ol202812d
  • Koduri ND, Wang Z, Cannel C, et al. Enaminones via ruthenium-catalyzed coupling of thioamides and α-diazocarbonyl compounds. J Org Chem. 2014;79:7405–7414. doi: 10.1021/jo5011312
  • Obijalska E, Blaszczyk M M, Kowalski MK, et al. A novel access to 4-trifluoromethyl-1,3-thiazole derivatives via an intermediate thiocarbonyl ylide. J Fluorine Chem. 2019;220:35–40. doi: 10.1016/j.jfluchem.2019.02.003
  • Honey MA, Pasceri R, Lewis W, et al. Diverse trifluoromethyl heterocycles from a single precursor. J Org Chem. 2012;77:1396–1405. doi: 10.1021/jo202201w
  • Fontrodona X, Díaz S, Linden A, et al. Copper(I) bromide-mediated synthesis of novel 2-arylthiazole-5-carboxylates from α-diazo-β-keto esters and aromatic thioamides. Synthesis (Mass). 2001;2021–2017. doi: 10.1055/s-2001-17697
  • Bachi MD, Goldberg O, Gross A, et al. Properties and reactions of 4-thioxo-2-azetidinones. J Org Chem. 1980;45:1481–1485. doi: 10.1021/jo01296a027
  • Medvedev JJ, Efimov IV, Shafran YM, et al. Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: a new entry for the synthesis of multisubstituted thiophenes. Beilstein J Org Chem. 2017;13:2569–2576. doi: 10.3762/bjoc.13.253
  • Egli DH, Linden A, Heimgartner H. 1,5-Dipolar electrocyclizations of thiocarbonyl ylides bearing C = N groups: reactions of N-[(dimethylamino)methylene]thiobenzamide and 2-(dimethylhydrazono)-1-phenylethane-1-thione with diazo compounds. Helv Chim Acta. 2007;90:86–100. doi: 10.1002/hlca.200790025
  • Song HM, Kim K. Rhodium(II)-mediated reactions of thiobenzoylketene S,N-acetals with α-diazocarbonyl compounds: synthesis of 2-substituted 3-alkylamino-5-phenylthiophenes. J Chem Soc, Perkin Trans 1. 2002: 2414–2417. doi: 10.1039/B203931A
  • Hamaguchi M, Funakoshi N, Oshima T. Reaction of vinylcarbenoids with thioketones: formation of vinylthiocarbonyl ylides followed by ring closure to thiiranes and dihydrothiophenes. Tetrahedron Lett. 1999;40:8117–8120. doi: 10.1016/S0040-4039(99)01716-5
  • Padwa A, Kinder FR, Zhi L. Generation of thiocarbonyl ylides from rhodium(II)-catalyzed cyclization of diazothiocarbonyl compounds. Synlett. 1991: 287–288. doi: 10.1055/s-1991-21980
  • Padwa A, Kinder FR, Nadler WR, et al. Rhodium(II) catalyzed cycloaddition of diazo thiocarbonyl compounds for heterocyclic synthesis. Heterocycles. 1993;35:367–383. doi: 10.3987/COM-92-S29
  • Kim G, Chu-Moyer MY, Danishefski SJ. Total synthesis of indolizomycin. J Am Chem Soc. 1990;112:2003–2005. doi: 10.1021/ja00161a059
  • Kim G, Chu-Moyer MY, Danishefski SJ, et al. The total synthesis of indolizomycin. J Am Chem Soc. 1993;115:30–39. doi: 10.1021/ja00054a005
  • Fang FG, Prato M, Kim G, et al. The aza-Robinson annulation: an application to the synthesis of iso-A58365A. Tetrahedron Lett. 1989;30:3625–3628. doi: 10.1016/S0040-4039(01)80465-2
  • Subba-Reddy BV, Babu RA, Reddy MR, et al. Intramolecular C–O/C–S bond insertion of α-diazoesters for the synthesis of 2-aryl-4H-benzo[d][1,3]oxazine and 2-aryl-4H-benzo[d][1,3]thiazine derivatives. RSC Adv. 2014;4:44629–44633. doi: 10.1039/C4RA08208G
  • Moody CJ, Slawin AMZ, Willows D. Dirhodium(II) tetraacetate catalysed reactions of diazothioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomünchnones), an approach to analogues of dehydrogliotoxin. Org Biomol Chem. 2003;1:2716–2722. doi: 10.1039/B305698H
  • Mlostoń G, Romański J, Schmidt C, et al. Photochemische und thermische Erzeugung von Thiocarbonylyliden aus 2,5-Dihydro-1,3,4-thiadiazolen. Chem Ber. 1994;127:2527–2530. doi: 10.1002/cber.19941271226
  • McGimpsey WG, Scaiano JC. Characterization of thiocabonyl ylides in the reaction of triplet carbenes with thioketones. Tetrahedron Lett. 1986;27:547–550. doi: 10.1016/S0040-4039(00)84036-8
  • Mlostoń G, Romański J, Heimgartner H. First synthesis of gem-difluorothiiranes from cycloaliphatic thioketones and difluorocarbene. Heterocycles. 1999;50:403–410. doi: 10.3987/COM-98-S(H)75
  • Mlostoń G, Romański J, Swiatek A, et al. Reactions of thioketones with dichlorocarbene. Helv Chim Acta. 1999;82:946–956. doi: 10.1002/(SICI)1522-2675(19990609)82:6<946::AID-HLCA946>3.0.CO;2-P
  • Shimada K, Sasaki J, Kishi A, et al. Synthesis of sterically-crowded olefins, gem-dihaloalkenes, butatrienes, and thioketenes through the reaction of substituted bornane-2-thiones or bornane-2-selones with conventional carbenes or metal carbenoids. Nat Prod Commun. 2013;8:851–858.
  • Tokitoh N, Suzuki T, Ando W. A facil synthesis and novel reactions of 1,2,3,4-pentatetraene episulfide. Tetrahedron Lett. 1989;30:4271–4274. doi: 10.1016/S0040-4039(01)80708-5
  • Tokitoh N, Hayakawa H, Ando W. New aspects in the tautomerism of 1,2,3-butatriene episulfides. Tetrahedron Lett. 1988;29:5161–5164. doi: 10.1016/S0040-4039(00)80708-X
  • Warkentin J. 2,5-Dihydro-1,3,4-oxadiazoles and Bis(heteroatom-substituted)carbenes. Acc Chem Res. 2009;42:205–213. doi: 10.1021/ar800072h
  • Reisenauer HP, Romański J, Mlostoń G, et al. Dimethoxycarbene: Conformational analysis of a reactive intermediate. Eur J Org Chem. 2006: 4813–4818. doi: 10.1002/ejoc.200600485
  • Dawid M, Mlostoń G, Warkentin J. The first 2,2-dialkoxythiirane. Org Lett. 2001;3:2455–2456. doi: 10.1021/ol016108g
  • Dawid M, Mlostoń G, Warkentin J. Relative reactivities of carbonyl and thiocarbonyl groups toward dimethoxycarbene: two new dimethoxythiiranes. Chem Eur J. 2002;8:2184–2167. doi: 10.1002/1521-3765(20020503)8:9<2184::AID-CHEM2184>3.0.CO;2-2
  • Dawid M, Reid DL, Warkentin J, et al. Reactions of dimethoxycarbene with carbon–sulfur double bonds. J Phys Org Chem. 2005;18:86–89. doi: 10.1002/poc.857
  • Dawid M, Mlostoń G, Reid DL, et al. Reactions of dimethoxycarbene with thiocarbonyl compounds. Can J Chem. 2003;81:1025–1028. doi: 10.1139/v03-124
  • Erian AW, Reid DL, Warkentin J. Reactions of dimethoxycarbene with xanthates. J Sulfur Chem. 2005;26:203–209. doi: 10.1080/17415990500208991
  • Mlostoń G, Kania K, Heimgartner H. Chemoselective insertion of dimethoxycarbene into the N–H bond of thiolactams with diverse ring size. J Sulfur Chem. 2009;30:278–286. doi: 10.1080/17415990902870935
  • Hoffmann RW S, Ditrich B. Addition von Dimethoxycarben an Isocyanate und isothiocyanate. Chem Ber. 1973;106:2174–2184. doi: 10.1002/cber.19731060711
  • Arduengo AJIII, Harlow RL, Kline MA. A stable crystalline carbene. J Am Chem Soc. 1991;113:361–363. doi: 10.1021/ja00001a054
  • Flanigan DM, Romanov-Michailidis F, White NA, et al. Organocatalytic reactions enabled by N-heterocyclic carbenes. Chem Rev. 2015;115:9307–9387. doi: 10.1021/acs.chemrev.5b00060
  • Nesterov V, Reiter D, Bag P, et al. NHCs in main group chemistry. Chem Rev. 2018;118:9678–9842. doi: 10.1021/acs.chemrev.8b00079
  • Krasuski W, Nikolaus D. Regitz M. Elektronenreiche Olefine, 6. CS2-Dipole aus elektronenreichen Olefinen – Herstellung und Cycloadditionsreaktionen. Liebigs Ann Chem. 1982: 1451–1465. doi: 10.1002/jlac.198219820805
  • Delaude L. Betaine adducts of N-heterocyclic carbenes: synthesis, properties, and reactivity. Eur J Inorg Chem. 2009: 1681–1699. doi: 10.1002/ejic.200801227
  • Beltran TF, Delaude L. Recent advances in small clusters and polymetallic assemblies based on transition metals and dithiocarboxylate zwitterions derived from N-heterocyclic carbenes. J Clust Sci. 2017;28:667–678. doi: 10.1007/s10876-017-1174-4
  • Awasti Ch, Yadav LDS. N-Heterocyclic carbene catalyzed [2 + 2]-cycloaddition of aryl isothiocyanates and nitroolefins: An efficient synthesis of β-thiolactams. Synlett. 2010: 1783–1788.
  • Ikota H, Ishida T, Ch T, et al. Synthesis of 3,3-disubstituted indoline-2-thiones catalysed by an N-heterocyclic carbene. Chem. Commun. 2014;50:8871–8874. doi: 10.1039/C4CC04047C
  • Fischer H, Treier K, Gebring J. Thiirane complexes from thioketones plus (CO)5W = C(Ph)H and diphenyldiazomethane plus (CO)5W[S = C(Ph)H]. J. Organomet Chem. 1992;433:127–133. doi: 10.1016/0022-328X(92)80135-K
  • Granados AM, Kreiker J, de Rossi GRH. Insertion of Fischer carbene complexes into the carbon-carbon bond. Ring expansion of a sulfur heterocycle from five- to six-membered. Tetrahedron Lett. 2002;43:8037–8041. doi: 10.1016/S0040-4039(02)01971-8
  • Granados AM, Kreiker J, de Rossi RH, et al. Synthesis of 1,3-dithiin dithioorthoesters from the reaction of Fischer carbenes and 3H-1,2-dithiole-3-thiones. J Org Chem. 2006;71:808–810. doi: 10.1021/jo052168e
  • Granados AM, Fracaroli AM, de Rossi RH, et al. Alkynyl Fischer carbene complex as a traceless directing group for the regioselective cycloaddition of dithiolethiones to arylacetylene: synthesis of E-dithiafulvene thione and dithioesters. Chem Commun. 2008: 483–485. doi: 10.1039/B715857B
  • Andrada DM, Granados AM, Solà M, et al. DFT study of thermal 1,3-dipolar cycloaddition reactions between alkynyl metal(0) Fischer carbene complexes and 3H-1,2-dithiole-3-thione derivatives. Organometallics. 2011;30:466–476. doi: 10.1021/om1007105
  • Joshua JL, Blavins DL, Karadakov PB. Spin-coupled study of addition reactions of singlet dihalocarbenes with ethene. Int J Quantum Chem. 2004;98:465–472. doi: 10.1002/qua.20081
  • Vogel P, Houk KN. Cyclopropanation by [2 + 1]-cheletropic addition of carbenes. In Reactivity and mechanisms in modern synthesis. Weinheim: Wiley – VCH Verlag, GmbH; 2019. Chapter 5.4.1, p. 437−439.
  • Mlostoń G, Celeda M, Jasiński M, et al. 2-Unsubstituted imidazole N-oxides as novel precursors of chiral 3-alkoxyimidazol-2-ylidenes derived from trans-1,2-diaminocyclohexane and other chiral amino compounds. Molecules. 2019;24:4398. doi: 10.3390/molecules24234398

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