PDF herunterladen
20.8. 13 Thiocarboxylic S -Acid, Selenocarboxylic Se -Acid, and Tellurocarboxylic Te -Acid Derivatives (Update 2024)
Buch
Herausgeber: Campagne, J.-M. ; Donohoe, T. J.; Jiang, X. ; Wang, M.
Titel: Knowledge Updates 2024/2
Online ISBN: 9783132457065; Buch-DOI: 10.1055/b000000968
1st edition © 2024 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
Science of Synthesis Knowledge Updates
Übergeordnete Publikation
Titel: Science of Synthesis
DOI: 10.1055/b-00000101
Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Typ: Mehrbändiges Werk
Abstract
Thiocarboxylic acid S-esters are synthetically versatile building blocks that can be smoothly interconverted into a wide array of valuable functional groups including aldehydes, ketones, carboxylic acids, and amides. This review, which is an update to an earlier Science of Synthesis contribution (Section 20.8), covers synthetic strategies to access thiocarboxylic acid S-esters and other derivatives, and primarily focuses on the literature published between 2006 and 2023. Additionally, robust methods to prepare seleno- and tellurocarboxylic acid esters, which are becoming widely used synthons in total synthesis and peptide chemistry, are highlighted.
Schlüsselwörter
thiocarboxylic acid S-esters - thiol surrogates - malonic acid half thioesters - N-to-S acyl transfer - hydrothiolation - sulfanylcarbonylation - C–S coupling- 2 Olivito F, Costanzo P, Di Gioia ML, Nardi M, Oliviero M, Propocia A. Org. Biomol. Chem. 2018; 16: 7753
- 13 Hu W.-F, Zhao J.-Q, Chen X.-Z, Zhou M.-Q, Zhang X.-M, Xu X.-Y, Yuan W.-C. Tetrahedron 2019; 75: 2206
- 17 Petracca R, Bowen KA, McSweeney L, O’Flaherty S, Genna V, Twamley B, Devocelle M, Scanlan EM. Org. Lett. 2019; 21: 3281
- 22 Van den Hoogenband A, Lange JHM, Bronger RPJ, Stoit AR, Terpstra JW. Tetrahedron Lett. 2010; 51: 6877
- 32 Sancineto L, Tidei C, Bagnoli L, Marini F, Lippolis V, Arca M, Lenardão EJ, Santi C. Eur. J. Org. Chem. 2016; 2999
- 33 Duarte A, Cunico W, Pereira CMP, Flores AFC, Freitag RA, Siqueira GM. Ultrason. Sonochem. 2010; 17: 281
- 36 Narayanaperumal S, Alberto EE, Gul K, Kawasoko CY, Dornelles L, Rodrigues OED, Braga AL. Tetrahedron 2011; 67: 4723
- 37 Tabarelli G, Alberto EE, Deobald AM, Marin G, Rodrigues OED, Dornelles L, Braga AL. Tetrahedron Lett. 2010; 51: 5728
- 63 Won J.-E, Kim H.-K, Kim J.-J, Yim H.-S, Kim M.-J, Kang S.-B, Chung H.-A, Lee S.-G, Yoon Y.-J. Tetrahedron 2007; 63: 12 720
- 76 Shi Y, Liu X, Cao H, Bie F, Han Y, Yan P, Szostak R, Szostak M, Liu C. Org. Biomol. Chem. 2021; 19: 2991
- 94 Hojo H, Kobayashi H, Ubagai R, Asahina Y, Nakahara Y, Katayama H, Ito Y, Nakahara Y. Org. Biomol. Chem. 2011; 9: 6807
- 97 Nakamura K, Mori H, Kawakami T, Hojo H, Nakahara Y, Aimoto S. Int. J. Pept. Res. Ther. 2007; 13: 191
- 116 Wang X, Wang B, Zin X, Yu W, Liao Y, Ye J, Wang M, Hu L, Liao J. Angew. Chem. Int. Ed. 2019; 58: 12 264
- 123 Iranpoor N, Firouzabadi H, Etemadi-Davan E, Nematollahi A, Firouzi HR. New J. Chem. 2015; 39: 6445
- 126 de Albuquerque DY, Teixeira WKO, do Sacramento M, Alves D, Santi C, Schwab RS. J. Org. Chem. 2022; 87: 595
- 147 Baldassari LL, Mantovani AC, Jardim M, Maryasin B, Lüdtke DS. Chem. Commun. (Cambridge) 2021; 57: 117
- 157 Downey CW, Dixon GJ, Ingersoll JA, Fuller CN, MacCormac KW, Takashima A, Sediqui R. Tetrahedron Lett. 2019; 60: 151 192
- 167 Hayashi Y, Yamada T, Sato M, Watanabe S, Kwon E, Iwasaki K, Umemiya S. Org. Lett. 2019; 21: 5183
- 171 Bew SP, Stephenson GR, Rouden J, Ashford P.-A, Bourane M, Charvet A, Dalstein VMD, Jauseau R, Hiatt-Gipson GD, Martinez-Lozano LA. Adv. Synth. Catal. 2015; 357: 1245
- 177 Bae HY, Some S, Lee JH, Kim J.-Y, Song JM, Lee S, Zhang YJ, Song CE. Adv. Synth. Catal. 2011; 353: 3196
- 179 Ricci A, Petterson D, Bernardi L, Fini F, Fochi M, Herrera RP, Sgarzani V. Adv. Synth. Catal. 2007; 349: 1037
- 200 Zeng J.-W, Liu Y.-C, Hsieh P.-A, Huang Y.-T, Yi C.-L, Badsara SS, Lee C.-F. Green Chem. 2014; 16: 2644
- 203 Guo S.-H, Wang M.-Y, Pan G.-F, Zhu X.-Q, Gao Y.-R, Wang Y.-Q. Adv. Synth. Catal. 2018; 360: 1861
- 204 Guo S.-H, Zhang X.-L, Pan G.-F, Zhu X.-Q, Gao Y.-R, Wang Y.-Q. Angew. Chem. Int. Ed. 2018; 57: 1663
- 214 Yan J, Tang H, Kuek EJR, Shi X, Liu C, Zhang M, Piper JL, Duan S, Wu J. Nat. Commun. 2021; 12: 7214
- 227 Maruani A, Lee MTW, Watkins G, Akhbar AR, Baggs H, Shamsabadi A, Richards DA, Chudasama V. RSC Adv. 2016; 6: 3372
- 231 Abenante L, Penteado F, Vieira MM, Perin G, Alves D, Lenardão EJ. Ultrason. Sonochem. 2018; 49: 41
- 240 Qi F, Yu H.-F, Wang Y.-N, Lv Y, Li Y.-X, Han L, Wang R, Feng X.-N. Synth. Commun. 2017; 47: 2220
- 254 Badsara SS, Liu Y.-C, Hsieh P.-A, Zeng J.-W, Lu S.-Y, Liu Y.-W, Lee C.-F. Chem. Commun. (Cambridge) 2014; 50: 11 374
- 263 Luo J, Rauch M, Avram L, Diskin-Posner Y, Schmul G, Ben-David Y, Milstein D. Nat. Catal. 2020; 3: 887
- 274 Tiecco M, Testaferri L, Temperini A, Bagnoli L, Marini F, Santi C, Terlizzi R. Eur. J. Org. Chem. 2004; 3447
- 276 Baldassari LL, Mantovani AC, Senoner S, Maryasin B, Maulide N, Lüdtke DS. Org. Lett. 2018; 20: 5881