17.8. 5 Porphyrins (Update 2022)
Book
Editors: Donohoe, T. J.; Krause, N.; Marsden, S. P.; Montchamp, J.-L.; Terent'ev, A. O. ; Weinreb, S. M.
Title: Knowledge Updates 2022/1
Print ISBN: 9783132451476; Online ISBN: 9783132451490; Book DOI: 10.1055/b000000641
1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: 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.
Type: Multivolume Edition
Abstract
This chapter covers methods for the synthesis and transformations of porphyrins, and is an update to the earlier Science of Synthesis contribution Section 17.8.1. The focus is on the literature published in the period 2000–2021. The basic principles and strategies for the construction and modification of the porphyrin core are examined, with an emphasis on the most useful approaches reported in the past two decades.
Key words
porphyrins - pyrroles - macrocycles - natural products - aldehydes - aromaticity - ring closure - total synthesis - acid catalysts - electrophilic substitution - aminoalkylation - Mannich reaction - Vilsmeier formylation-
11 Stillman MJ, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2011; 14. 461–524
-
12 Waluk J, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2010; 7. 359–435
-
13 Medforth CJ, In: The Porphyrin Handbook Kadish KM, Smith KM, Guilard R. Academic Amsterdam 2000; 5. 1–80
-
14 Quirke JME, In: The Porphyrin Handbook: Kadish KM, Smith KM, Guilard R. Academic Amsterdam 2000; 7. 371–422
-
16 Brückner C, Samankumara LP, Ogikubo J, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2012; 17. 1–112
-
17 Layer G, Warren MJ, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2012; 19. 111–138
- 23 Willstätter R, Stoll A. Untersuchungen über Chlorophyll. Methoden und Ergebnisse. Springer; Berlin 1913: 424
-
26 Woodward RB, Ayer WA, Beaton JM, Bickelhaupt F, Bonnett R, Buchschacher P, Closs GL, Dutler H, Hannah J, Hauck FP, Itǒ S, Langemann A, LeGoff E, Leimgruber W, Lwowski W, Sauer J, Valenta Z, Volz H. J. Am. Chem. Soc. 1960; 82: 3800
-
27 Woodward RB, Ayer WA, Beaton JM, Bickelhaupt F, Bonnett R, Buchschacher P, Closs GL, Dutler H, Hannah J, Hauck FP, Itǒ S, Langemann A, LeGoff E, Leimgruber W, Lwowski W, Sauer J, Valenta Z, Volz H. Tetrahedron 1990; 46: 7599
-
28 Callot HJ, Ocampo R, In: The Porphyrin Handbook Kadish KM, Smith KM, Guilard R. Academic Amsterdam 2000; 1. 349–398
- 29 Biogeochemistry of Ancient and Modern Environments. Trudinger PA, Walter MR, Ralph BJ. Springer; Berlin 1980
-
34 Leeper FJ, Warren MJ, Kelly JM, Lawrence AD, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2012; 25. 1–81
-
35 Shoolingin-Jordan P, In: The Porphyrin Handbook Kadish KM, Smith KM, Guilard R. Elsevier Amsterdam 2003; 12. 33–74
-
36 Scott AI, Roessner CA, Santander PJ, In: The Porphyrin Handbook Kadish KM, Smith KM, Guilard R. Elsevier Amsterdam 2003; 12. 211–228
-
38 Ono N, Yamada H, Okujima T, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2010; 2. 1–102
-
39 Cavaleiro JAS, Tomé AC, Neves MariaGPMS, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2010; 2. 193–294
-
40 Beletskaya IP, Tyurin VS, Uglov A, Stern C, Guilard R, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2012; 23. 81–279
-
42 Drain CM, Singh S, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2010; 3. 485–537
-
43 Taniguchi M, Lindsey JS, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2012; 23. 1–80
-
47 Lindsey JS, In: The Porphyrin Handbook Kadish KM, Smith KM, Guilard R. Academic New York 2000; 1. 45–118
- 63 Fischer H, Orth H. Die Chemie des Pyrrols. Akademische Verlagsgesellschaft; Leipzig 1937. 2. 160–173
-
65 Bauer VJ, Clive DLJ, Dolphin D, Paine III JB, Harris FL, King MM, Loder J, Wang SWC, Woodward RB. J. Am. Chem. Soc. 1983; 105: 6429
-
70 Lash TD, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2012; 16. 1–329
-
71 Pawlicki M, Latos-Grazynski L, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2010; 2. 103–192
-
72 Brückner C, Götz DCG, Fox SP, Ryppa C, McCarthy JR, Bruhn T, Akhigbe J, Banerjee S, Daddario P, Daniell HW, Zeller M, Boyle RW, Bringmann G. J. Am. Chem. Soc. 2011; 133: 8740
-
73 Brückner C, Akhigbe J, Samankumara LP, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2014; 31. 1–275
-
75 Smith KM, In: The Porphyrin Handbook Kadish KM, Smith KM, Guilard R. Academic San Diego 2000; 1. 1–43
-
92 Borbas KE, In: Handbook of Porphyrin Science Kadish KM, Smith KM, Guilard R. World Scientific Singapore 2016; 36. 1–149
-
107 Adams KR, Berenbaum MC, Bonnett R, Nizhnik AN, Salgado A, Valles MA. J. Chem. Soc., Perkin Trans. 1 1992; 1465
-
111 Sergeeva NN, Senge MO, Ryan A, In: Handbook of Porphyrin Science Kadish KM, Guilard R, Smith KM. World Scientific Singapore 2010; 3. 325–365
-
113 Fields KB, Ruppel JV, Snyder NL, Zhang XP, In: Handbook of Porphyrin Science Kadish KM, Guilard R, Smith KM. World Scientific Singapore 2010; 3. 367–427
-
115 Jaquinod L, In: The Porphyrin Handbook Kadish KM, Smith KM, Guilard R. Academic New York 2000; 1. 201–237
-
116 Senge MO, In: The Porphyrin Handbook Kadish KM, Smith KM, Guilard R. Academic New York 2000; 1. 239–347
-
119 Chumakov DE, Khoroshutin AV, Anisimov AV, Kobrakov KI. Chem. Heterocycl. Compd. (Engl. Transl.) 2009; 45: 259
-
134 Bonfantini EE, Burrell AK, Campbell WM, Crossley MJ, Gosper JJ, Harding MM, Officer DL, Reid DCW. J. Porphyrins Phthalocyanines 2002; 6: 708
-
139 Pereira MM, Muller G, Ordinas JI, Azenha ME, Arnaut LG. J. Chem. Soc., Perkin Trans. 2 2002; 1583
-
140 Sergeeva NN, Scala A, Bakar MA, O’Riordan G, O’Brien J, Grassi G, Senge MO. J. Org. Chem. 2009; 74: 7140
-
142 Shanmugathasan S, Johnson CK, Edwards C, Matthews EK, Dolphin D, Boyle RW. J. Porphyrins Phthalocyanines 2000; 4: 228