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Photocatalyzed Formation of Heterocycles Read chapter Read first chapter

2018 | OriginalPaper | Chapter

Heteroatom-Centred Radicals for the Synthesis of Heterocyclic Compounds

Author : Fabrice Dénès

Published in: Free-Radical Synthesis and Functionalization of Heterocycles

Publisher: Springer International Publishing

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Abstract

An overview of the synthetic methods allowing the preparation of heterocyclic structures based upon the use of heteroatom-centred radicals (R–X•) is presented here. The discussion will be limited to specific examples for which the heteroatom (X = SiR2, GeR2, SnR2, PR, NR, O, S, SO2, Se) is included in the heterocyclic structure itself during the cyclisation process leading to its formation. These include the cyclisation of heteroatom-centred radicals onto unsaturated partners such as alkenes, alkynes, arenes, ketones or nitriles and the formation of the heterocycle via a sequence involving remote functionalisation reactions leading to halogenated intermediates, followed by ionic cyclisation (e.g. Hofmann–Löffler–Freytag reaction), as well as cascade reactions terminating with an intramolecular homolytic substitution (SHi) at the heteroatom in the final step.

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previous chapter Free Radicals in Heterocycle Functionalization
next chapter Metal-Mediated Oxidative Radical Processes for the Synthesis of Heterocycles
Literature
1.
Landais Y (2013) In: Bellus D, Ley S, Noyori R, Trost B (eds) Science of synthesis. G. Thieme, vol 26
2.
3.
Ballestri M, Chatgilialoglu C, Clark KB, Griller D, Giese B, Kopping B (1991) J Org Chem 56:678CrossRef
4.
5.
6.
7.
8.
Ballestri M, Chatgilialoglu C, Guerra M, Guerrini A, Lucarini M, Seconi G (1993) J Chem Soc Perkin Trans 2:421CrossRef
9.
10.
11.
12.
13.
14.
15.
16.
17.
Sakurai H (1973) In: Kochi J (ed) Free radicals, vol 2. Wiley, New York
18.
Chatgilialoglu C, Woynar H, Ingold KU, Davies AG (1983) J Chem Soc Perkin Trans 2:555CrossRef
19.
20.
21.
22.
23.
24.
25.
Ishibashi H, Sato T, Ikeda M (2002) Synthesis:695
26.
27.
Clive DLJ, Cantin M (1995) J Chem Soc Chem Commun:319
28.
29.
30.
31.
32.
33.
34.
Schiesser CH, Matsubara H, Ritsner I, Wille U (2006) Chem Commun:1067
35.
36.
37.
38.
39.
Kulicke K, Chatgilialoglu CS, Kopping B, Iese B (1992) Helv Chim Acta 75:935CrossRef
40.
41.
42.
Ryu I, Kurihara A, Muraoka H, Tsunoi S, Kambe N, Sonoda N (1994) J Org Chem 59:7570CrossRef
43.
44.
Rouquet G, Robert F, Méreau R, Castet F, Renaud P, Landais Y (2012) Chem A Eur J 18:940CrossRef
45.
46.
Beckwith ALJ, Roberts DH, Schiesser CH, Wallner A (1985) Tetrahedron Lett 26:3349CrossRef
47.
48.
49.
50.
51.
Allard N, Aïch RB, Gendron D, Boudreault P-LT, Tessier C, Alem S, Tse S-C, Tao Y, Leclerc M (2010) Macromolecules 43:2328CrossRef
52.
53.
54.
55.
56.
Kamimura A, Ishikawa S, Noguchi F, Moriyama T, So M, Murafuji T, Uno H (2012) Chem Commun 48:6592CrossRef
57.
Kamimura A, Yoshinaga T, Noguchi F, Miyazaki K, Uno H (2015) Org Chem Front 2:713CrossRef
58.
59.
60.
61.
62.
63.
64.
65.
66.
Esker JL, Newcomb M (1993) In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 58. Academic Press, New York, p 1
67.
68.
69.
70.
71.
72.
73.
Li Y, Wang R, Wang T, Cheng X-F, Zhou X, Fei F, Wang X-S (2017) Angew Chem Int Ed 56:15436CrossRef
74.
75.
Hu X-Q, Chen J-R, Wei Q, Liu F-L, Deng Q-H, Beauchemin AM, Xiao W-J (2014) Angew Chem Int Ed 53:12163CrossRef
76.
77.
78.
79.
Zhao Q-Q, Hu X-Q, Yang M-N, Chen J-R, Xiao W-J (2016) Chem Commun 52:12749
80.
81.
82.
83.
84.
85.
86.
87.
Bowman WR, Broadhurst MJ, Coghlan DR, Lewis KA (1997) Tetrahedron Lett 38:6301CrossRef
88.
89.
Zhai H, Wickenden JG, Sammis GM (2010) Synlett:3035
90.
Zhai H, Zlotorzynska M, Sammis G (2009) Chem Commun:5716
91.
92.
93.
94.
95.
Sjoholm A, Hemmerling M, Pradeille N, Somfai P (2001) J Chem Soc Perkin Trans 1:891CrossRef
96.
Senboku H, Kajizuka Y, Hasegawa H, Fujita H, Suginome H, Orito K, Tokuda M (1999) Tetrahedron 55:6465CrossRef
97.
98.
99.
100.
101.
102.
103.
104.
105.
106.
Benati L, Bencivenni G, Leardini R, Minozzi M, Nanni D, Scialpi R, Spagnolo P, Zanardi G, Rizzoli C (2004) Org Lett 6:417PubMedCrossRef
107.
Benati L, Bencivenni G, Leardini R, Nanni D, Minozzi M, Spagnolo P, Scialpi R, Zanardi G (2006) Org Lett 8:2499PubMedCrossRef
108.
Narasaka K, Kitamura M (2005) Eur J Org Chem:4505
109.
110.
111.
112.
113.
114.
Le Tadic-Biadatti M-H, Callier-Dublanchet A-C, Horner JH, Quiclet-Sire B, Zard SZ, Newcomb M (1997) J Org Chem 62:559PubMedCrossRef
115.
Morimoto T, Nezu T, Achiwa T, Sekia M (1985) J Chem Soc Chem Commun:1584
116.
117.
118.
119.
120.
121.
Forrester AR, Gill M, Sadd JS, Thomson RH (1975) J Chem Soc Chem Commun:291
122.
123.
124.
125.
126.
127.
Duan X-Y, Zhou N-N, Fang R, Yang X-L, Yu W, Han B (2014) Angew Chem Int Ed 53:3158CrossRef
128.
Asensio G, Gonzalez-Nunez E, Rodrigo MJ (1987) J Chem Soc Chem Commun:263
129.
130.
Zhu L, Xiong P, Mao Z-Y, Wang Y-H, Yan X, Lu X, Xu H-C (2016) Angew Chem Int Ed 55:2226CrossRef
131.
Folgueiras-Amador AA, Philipps K, Guilbaud S, Poelakker J, Wirth T (2017) Angew Chem Int Ed 56:15446CrossRef
132.
133.
134.
135.
136.
137.
138.
139.
140.
141.
142.
143.
144.
145.
146.
Clark AJ, Deeth RJ, Samuel CJ, Wongtap H (1999) Synlett:444
147.
148.
149.
150.
Boivin J, Callier-Dublanchet A-C, Quiclet-Sire B, Schiano A-M, Zard SZ (1995) Tetrahedron 51:6517CrossRef
151.
152.
153.
Callier-Dublanchet A-C, Cassayre J, Gagosz F, Quiclet-Sire B, Sharp LA, Zard SZ (2008) Tetrahedron 64:4803CrossRef
154.
Biechy A, Hachisu S, Quiclet-Sire B, Ricard L, Zard SZ (2008) Angew Chem Int Ed 47:1436CrossRef
155.
Biechy A, Hachisu S, Quiclet-Sire B, Ricard L, Zard SZ (2009) Tetrahedron 65:6730CrossRef
156.
157.
Moutrille C, Zard SZ (2004) Chem Commun:1848
158.
159.
160.
161.
162.
Clark AJ, Filik RP, Paecock JL, Thomas GH (1999) Synlett:441
163.
164.
Reina DF, Dauncey EM, Morcillo SP, Svejstrup TD, Popescu MV, Douglas JJ, Sheikh NS, Leonori D (2017) Eur J Org Chem:2108
165.
166.
167.
Weinberg DR, Gagliardi CJ, Hull JF, Murphy CF, Kent CA, Westlake BC, Paul A, Ess DH, McCafferty DG, Meyer TJ (2012) Chem Rev 112:4016PubMedCrossRef
168.
169.
170.
171.
Li S-Q, Xiong P, Zhu L, Qian X-Y, Xu H-C (2016) Eur J Org Chem:3449
172.
Xiong P, Xu F, Qian X-Y, Yohannes Y, Song J, Lu X, Xu H-C (2016) Chem A Eur J 22:4379CrossRef
173.
Nicolaou KC, Baran PS, Kranich R, Zhong Y-L, Sugita K, Zou N (2001) Angew Chem Int Ed 40:202CrossRef
174.
175.
176.
177.
178.
179.
180.
Feray L, Kuznetsov N, Renaud P (2001) In: Renaud P, Sibi MP (eds) Radicals in organic synthesis, vol 2. Wiley-VCH, Weinheim, p 246
181.
182.
183.
184.
Hernandez R, Rivera A, Salazar JA, Suarez E (1980) J Chem Soc Chem Commun:958
185.
Betancor C, Concepcion JI, Hernandez R, Salazar JA, Suarez E (1983) J Org Chem 48:4430CrossRef
186.
Freire R, Martın A, Pérez-Martın I, Suárez E (2002) Tetrahedron Lett 43:5113CrossRef
187.
Francisco CG, Herrera AJ, Martín Á, Pérez-Martín I, Suárez E (2007) Tetrahedron Lett 48:6384CrossRef
188.
189.
León EI, Martín Á, Pérez-Martín I, Suárez E (2011) Eur J Org Chem:7339
190.
191.
192.
193.
194.
195.
196.
197.
198.
Becker P, Duhamel T, Stein CJ, Reiher M, Muñiz K (2017) Angew Chem Int Ed 56:8004CrossRef
199.
200.
201.
Barton DHR, Beckwith ALJ, Goosen A (1965) J Chem Soc:181
202.
Hernández R, Medina MC, Salazar JA, Suárez E, Prangé T (1987) Tetrahedron Lett 28:2533CrossRef
203.
204.
205.
Forrester AR, Gill M, Napier RJ, Thomson RH (1979) J Chem Soc Perkin Trans 1:632CrossRef
206.
207.
208.
Espinal-Viguri M, King AK, Lowe JP, Mahon MF, Webster RL (2016) ACS Catal 6:7892CrossRef
209.
Davies AG, Parrott MJ, Roberts BP (1974) J Chem Soc Chem Commun:27
210.
211.
212.
Krech F, Issleib K, Zschunke A, Mügge C, Skvorcov S (1991) Z Anorg Allg Chem 594:66CrossRef
213.
214.
215.
Krauss B, Mügge C, Zschunke A, Krech F, Flock M (2002) Z Anorg Allg Chem 628:580CrossRef
216.
217.
Robertson A, Bradaric C, Frampton CS, McNulty J, Capretta A (2001) Tetrahedron Lett 42:2609CrossRef
218.
219.
220.
Beckwith ALJ, Hay BP, Williams GM (1989) J Chem Soc Chem Commun:1202
221.
222.
223.
224.
225.
Yokota M, Toyota M, Ihara M (2003) Chem Commun:422
226.
227.
228.
229.
230.
231.
232.
233.
234.
235.
Hartung J, Kneuer R, Kopf TM, Schmidt P (2001) Compt Rend Acad Sci Series IIC Chem 4:649
236.
Hartung J, Gottwald T, Špehar K (2003) Synlett:227
237.
238.
Schur C, Becker N, Bergsträßer U, Gottwald T, Hartung J (2011) Tetrahedron 67:2338CrossRef
239.
Gottwald T, Greb M, Hartung J (2004) Synlett:65
240.
Hartung J, Kneuer R, Laug S, Schmidt P, Špehar K, Svoboda I, Fuess H (2003) Eur J Org Chem:4033
241.
Hartung J, Daniel K, Bergsträßer U, Kempter I, Schneiders N, Danner S, Schmidt P, Svoboda I, Fuess H (2009) Eur J Org Chem:4135
242.
Hartung J, Schwarz M, Svoboda I, Fuess H, Duarte MT (1999) Eur J Org Chem:1275
243.
244.
245.
Barton DHR, Motherwell RSH, Motherwell WB (1981) J Chem Soc Perkin Trans 1:2363CrossRef
246.
247.
248.
249.
Dénès F, Beaufils F, Renaud P (2008) Synlett:2389
250.
251.
252.
253.
254.
255.
256.
257.
258.
259.
260.
Togo H (2004) In: Advanced free radical reactions for organic synthesis. Elsevier Science, Amsterdam, p 171CrossRef
261.
262.
263.
264.
265.
266.
267.
Petrovic G, Čeković Ž (2004) Synthesis:1671
268.
269.
270.
271.
272.
273.
274.
275.
276.
Danishefsky SJ, Armistead DM, Wincott FE, Selnick HG, Hungate R (1987) J Am Chem Soc 109:8117CrossRef
277.
Francisco CG, Freire R, Hernández R, Medina MC, Suárez E (1983) Tetrahedron Lett 24:4621CrossRef
278.
Concepción JI, Francisco CG, Hernández R, Salazar JA, Suárez E (1984) Tetrahedron Lett 25:1953CrossRef
279.
280.
Francisco CG, Herrera AJ, Kennedy AR, Melián D, Suárez E (2002) Angew Chem Int Ed 41:856CrossRef
281.
282.
283.
Alvarez-Dorta D, León EI, Kennedy AR, Martín A, Pérez-Martín I, Suárez E (2015) Angew Chem Int Ed 54:3674CrossRef
284.
Alvarez-Dorta D, León EI, Kennedy AR, Martín A, Pérez-Martín I, Suárez E (2016) J Org Chem 81:11766PubMedCrossRef
285.
Tsunoi S, Ryu I, Okuda T, Tanaka M, Komatsu M, Sonoda N (1998) J Am Chem Soc 120:8692CrossRef
286.
287.
288.
289.
290.
291.
292.
293.
Gao L, Zackert WE, Hasford JJ, Danekis ME, Milne GL, Remmert C, Reese J, Yin H, Tai H-H, Dey SK, Porter NA, Morrow JD (2003) J Biol Chem 278:28479PubMedCrossRef
294.
295.
296.
297.
298.
299.
300.
301.
Beckwith ALJ, Wagner RD (1980) J Chem Soc Chem Commun:485
302.
303.
Wang X, Ni Z, Lu X, Smith TY, Rodriguez A, Padwa A (1992) Tetrahedron Lett 33:5917CrossRef
304.
Wang X, Ni Z, Liu X, Hollis A, Blanks H, Rodriguez A, Padwa A (1993) J Org Chem 58:5377CrossRef
305.
306.
307.
308.
309.
310.
Bachi MD, Korshin EE, Ploypradith P, Cumming JN, Xie S, Shapiro TA, Posner GH (1998) Bioorg Med Lett 8:903CrossRef
311.
312.
313.
Korshin EE, Hoos R, Szpilman AM, Konstantinovski L, Posner GH, Bachi MD (2002) Tetrahedron 58:2449CrossRef
314.
Bachi MD, Korshin EE, Hoos R, Szpilman AM, Ploypradith P, Xie S, Shapiro TA, Posner GH (2003) J Med Chem 46:2516PubMedCrossRef
315.
O’Neill PM, Stocks PA, Pugh MD, Araujo NC, Korshin EE, Bickley JF, Ward SA, Bray PG, Pasini E, Davies J, Verissimo E, Bachi MD (2004) Angew Chem Int Ed 43:4193CrossRef
316.
317.
Feldman KS, Simpson RE (1989) J Am Chem Soc 111:4878
318.
319.
320.
321.
322.
323.
324.
Han B, Yang X-L, Fang R, Yu W, Wang C, Duan X-Y, Liu S (2012) Angew Chem Int Ed 51:8816CrossRef
325.
326.
327.
328.
329.
Chatgilialoglu C, Guerra M (1993) In: Patai S, Rappoport Z (eds) Supplement S: the chemistry of sulfur-containing functional groups. Wiley, Chichester, p 363
330.
Chatgilialoglu C, Bertrand MP, Ferreri C (1999) In: Alfassi ZB (ed) S-centered radicals. Wiley, Chichester, p 310
331.
von Sonntag C (1990) In: Chatgilialoglu C, Asmus K-D (eds) Sulfur-centered reactive intermediates in chemistry and biology. Plenum Press, New York, p 359
332.
333.
334.
335.
336.
ten Brummelhuis N, Schlaad H (2012) In: Chatgilialoglu C, Studer A (eds) Encyclopedia of radicals in chemistry, biology and materials, polymers and materials, vol 4. Wiley, Chichester, p 2017
337.
338.
McSweeney L, Dénès F, Scanlan EM (2016) Eur J Org Chem:2080
339.
340.
341.
342.
343.
344.
Surzur J-M, Crozet MP, Dupuy C (1967) Compt Rend Acad Sci Série C 264:610
345.
346.
347.
348.
Bastien G, Surzur J-M (1979) Bull Soc Chim Fr:601
349.
Bastien G, Crozet MP, Flesia E, Surzur J-M (1979) Bull Soc Chim Fr:606
350.
Surzur J M; Abramovitch R A, Ed.; Plenum Press: New York, 1982; 2, p 121
351.
352.
Surzur J-M, Crozet MP (1969) Compt Rend Acad Sci 268C:2109
353.
Kaafarani M, Crozet MP, Surzur J-M (1981) Bull Soc Chim Fr II:449
354.
Crozet MP, Kaafarani M, Kassar W, Surzur J-M (1982) Tetrahedron Lett 23:5039CrossRef
355.
Crozet MP, Kaafarani M, Surzur J-M (1984) Bull Soc Chim Fr II:390
356.
Crozet MP, Kassar W (1985) Compt Rend Acad Sci 300:99
357.
Kaafarani M, Crozet MP, Surzur J-M (1987) Bull Soc Chim Fr:885
358.
359.
360.
361.
362.
363.
Maki Y, Sako M (1978) J Chem Soc Chem Commun:836
364.
365.
366.
367.
368.
369.
370.
371.
Ichinose Y, Wakamatsu K, Nozaki K, Birbaum J-L, Oshima K, Utimoto K (1987) Chem Lett 16:1647
372.
373.
374.
375.
Sukhomazova EN, Russavskaya NV, Kozchevin NA, Deryagina EN, Voronkov MG (1989) Zh Org Khim 25:1506
376.
377.
378.
379.
380.
381.
Nanni D, Calestani G, Leardini R, Zanardi G (2000) Eur J Org Chem:707
382.
383.
Harrowven DC, Hannam JC, Lucas MC, Newman NA, Howes PD (2000) Tetrahedron Lett 41:9345CrossRef
384.
385.
386.
387.
388.
389.
390.
Bertrand F, Le Guyader F, Liguori L, Ouvry G, Quiclet-Sire B, Seguin S, Zard SZ (2001) Compt Rend Acad Sci Series IIC Chem 4:547
391.
392.
393.
394.
395.
396.
397.
398.
Ashcroft MR, Bougeard P, Bury A, Cooksey CJ, Johnson MD, Hungerford JM, Lampman GM (1984) J Org Chem 49:1751CrossRef
399.
400.
Xiao X, Xu Z, Zeng Q-D, Chen X-B, Ji W-H, Han Y, Wu P, Ren J, Zeng B-B (2015) Chem A Eur J 21:8351CrossRef
401.
Orlov YD, Turovtsev VV, Stepnikov IV, Kizin AN, Lebedev YA (2004) Russ Chem Bull 53:1635CrossRef
402.
403.
Bhuyan BJ, Mugesh G (2011) In: Organoselenium chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, p 361
404.
Harwood LM, Moody CJ (1999) In: Back TG (ed) The practical approach in chemistry series: organoselenium chemistry. Oxford University Press, New York, NY
405.
Wirth T (ed) (2012) Organoselenium chemistry: synthesis and reactions. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
406.
Bowman WR (2011) In: Organoselenium chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, p 111
407.
Ogawa A, Yokoyama H, Yokoyama K, Masawaki T, Kambe N, Sonoda N (1991) J Org Chem 56:5721CrossRef
408.
409.
410.
411.
412.
413.
Kumar S, Johansson H, Engman L, Valgimigli L, Amorati R, Fumo MG, Pedulli GF (2007) J Org Chem 72:2583PubMedCrossRef
414.
415.
416.
417.
418.
419.
420.
421.
422.
423.
Macdougall PE, Aitken HM, Scammells PJ, Kavanagh Y, Kyne SH, Schiesser CH (2012) Chem Commun 48:9126CrossRef
424.
425.
426.
Metadata
Title
Heteroatom-Centred Radicals for the Synthesis of Heterocyclic Compounds
Author
Fabrice Dénès
Copyright Year
2018
Book
Free-Radical Synthesis and Functionalization of Heterocycles

Print ISBN: 978-3-319-89520-8

Electronic ISBN: 978-3-319-89521-5

Copyright Year: 2018

DOI
https://doi.org/10.1007/7081_2018_19

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