Modern developments in aryl radical chemistry

Topics in Current Chemistry

Volumn 320, Issue , 2012, Pages 33-59

  Pratsch, Gerald ^a   Heinrich, Markus R ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Aryl radicals; Natural products; Radical addition; Radical cyclization

Indexed keywords

AROMATIC HYDROCARBON; FREE RADICAL; ORGANOMETALLIC COMPOUND; TIN;

CATALYSIS; CHEMISTRY; REVIEW;

CATALYSIS; FREE RADICALS; HYDROCARBONS, AROMATIC; ORGANOMETALLIC COMPOUNDS; TIN;

EID: 84858125346     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2011_127     Document Type: Review

References (163)

1. Griess P (1866) Justus Liebig Ann 137:39
2. Gomberg M (1900) J Am Chem Soc 22:757
3. Sandmeyer T (1884) Chem Ber 17:1633
4. Pschorr R (1896) Chem Ber 29:496
5. Gomberg M, Bachmann WE (1924) J Am Chem Soc 46:2339
6. Meerwein H, Buchner E, Emster Kv (1939) J Prakt Chem 152:237
7. Galli C (1988) Chem Rev 88:765
8. Walters WA (1967) The chemistry of free radicals. Wiley, Boca Raton
9. Zollinger H (1973) Acc Chem Res 6:335
10. Cohen T, Lewarchik RJ, Tarino JZ (1974) J Am Chem Soc 96:7753
11. Cohen T, Dietz AG, Miser JR (1977) J Org Chem 42:2053
12. Kerk GM (1957) J Appl Chem 356
13. Studer A, Bossart M (2001) In: Renaud P, Sibi M (eds) Radicals in organic synthesis, 2nd edn. Wiley-VCH, Weinheim
14. Bowman WR, Storey JMD (2007) Chem Soc Rev 36:1803
15. Vaillard SE, Schulte B, Studer A (2009) In: Ackermann L (ed) Modern arylation methods. Wiley-VCH, Weinheim
16. Majumdar KC, Basu PK, Mukhopadhyay PP (2005) Tetrahedron 61:10603
17. Majumdar KC, Basu PK, Chattopadhyay SK (2007) Tetrahedron 63:793
18. Beckwith ALJ, Meijs GF (1987) J Org Chem 52:1922
19. Bhandal H, Patel VF, Pattenden G, Russell JJ (1990) J Chem Soc Perkin Trans 110:2691
20. Meijs GF, Beckwith ALJ (1986) J Am Chem Soc 108:5890
21. Beckwith ALJ, Gara WB (1975) J Chem Soc Perkin Trans 2 795
22. Beckwith ALJ, Meijs GF (1981) J Chem Soc Chem Commun 3:136
23. Petrillo G, Novi M, Garbarino G, Filiberti M (1988) Tetrahedron Lett 29:4185
24. Fletcher RJ, Lampard C, Murphy JA, Lewis N (1995) J Chem Soc Perkin Trans 1 6:623
25. Koizumi T, Bashir N, Murphy JA (1997) Tetrahedron Lett 38:7635
26. Koizumi T, Bashir N, Kennedy AR, Murphy JA (1999) J Chem Soc Perkin Trans 124:3637
27. Togo H, Kikuchi O (1988) Tetrahedron Lett 29:4133
28. Liu Y, Schwartz J (1995) Tetrahedron 51:4471
29. Perchyonok VT, Tuck KL, Langford SJ, Hearn MW (2008) Tetrahedron Lett 49:4777
30. Abeywickrema AN, Beckwith ALJ (1986) Tetrahedron Lett 27:109
31. Boivin J, Camara J, Zard SZ (1992) J Am Chem Soc 114:7909
32. Totleben MJ, Curran DP, Wipf P (1992) J Org Chem 57:1740
33. Curran DP, Totleben MJ (1992) J Am Chem Soc 114:6050
34. Molander GA, Harring LS (1990) J Org Chem 55:6171
35. Patel VF, Pattenden G (1987) Tetrahedron Lett 28:1451
36. Martin GC, Murphy JA, Smith CR (2000) Tetrahedron Lett 41:1833
37. Mahesh M, Murphy JA, LeStrat F, Wessel HP (2009) Beilstein J Org Chem 5(1)
38. Murphy JA, Khan TA, Zhou S, Thomson DW, Mahesh M (2005) Angew Chem Int Ed 44:1356
39. Fukuyama T, Kobayashi M, Rahman MT, Kamata N, Ryu I (2008) Org Lett 10:533
40. Alabugin IV, Manoharan M (2005) J Am Chem Soc 127:12583
41. Ishibashi H, Kobayashi T, Nakashima S, Tamura O (2000) J Org Chem 65:9022
42. Curran D, Fairweather M (2003) J Org Chem 68:2972
43. Kamimura A, Ishihara Y, So M, Hayashi T (2009) Tetrahedron Lett 50:1727
44. De la Fuente MC, Dominguez D (2007) J Org Chem 72:8804
45. Navarro-Vázquez A, Garcia A, Dominguez D (2002) J Org Chem 67:3213
46. Petit M, Lapierre AJB, Curran DP (2005) J Am Chem Soc 127:14994
47. Petit M, Geib SJ, Curran DP (2004) Tetrahedron 60:7543
48. Majumdar KC, Alam S (2006) Org Lett 8:4059
49. Dandapani S, Duduta M, Panek JS, Porco JA Jr (2007) Org Lett 9:3849
50. Sato A, Yorimitsu H, Oshima K (2006) J Am Chem Soc 128:4240
51. Vaillard SE, Mueck-Lichtenfeld C, Grimme S, Studer A (2007) Angew Chem Int Ed 46:6533
52. Beckwith ALJ, Wang S, Warkentin J (1987) J Am Chem Soc 109:5289
53. Beak P, Park YS, Reif LA, Liu C (1994) J Org Chem 59:7410
54. Viswanathan R, Prabhakaran EN, Plotkin MA, Johnston JN (2003) J Am Chem Soc 125:163
55. McClure CK, Kiessling AJ, Link JS (1998) Tetrahedron 54:7121
56. Tomaszewski MJ, Warkentin J (1992) Tetrahedron Lett 33:2123
57. Johnston JN, Plotkin MA, Viswanathan R, Prabhakaran EN (2001) Org Lett 3:109
58. Viswanathan R, Smith CR, Prabhakaran EN, Johnston JN (2008) J Org Chem 73:3040
59. Coulomb J, Certal V, Fentserbank L, Lacôte E, Malacria M (2006) Angew Chem Int Ed 45:633
60. Benati L, Leardini R, Minozzi M, Nanni D, Spagnolo P, Strazzari S, Zanardi G (2002) Org Lett 4:3079
61. Oii T, Furuya M, Sakai D, Maruoka K (2001) Adv Synth Catal 343:166
62. Carta P, Puljic N, Robert C, Dhimane AL, Fensterbank L, Lacôte E, Malacria M (2007) Org Lett 9:1061
63. Hilton ST, Ho TCT, Pljevaljcic G, Schulte M, Jones K (2001) Chem Commun 2:209
64. Rey V, Pierini AB, Penénory AB (2009) J Org Chem 74:1223
65. Amrein S, Bossart M, Vasella T, Studer A (2000) J Org Chem 65:4281
66. Schiesser CH, Sutej K (1992) Tetrahedron Lett 33:5137
67. Engman L, Laws MJ, Malmstrom J, Schiesser CH, Zugaro LM (1999) J Org Chem 64:6764
68. Laws MJ, Schiesser CH (1997) Tetrahedron Lett 38:8429
69. Bowman WR, Fletcher AJ, Potts GBS (2002) J Chem Soc Perkin Trans 1 2747
70. Ikeda M, Ohtani S, Sato T, Ishibashi H (1998) Synthesis 12:1803
71. Patro B, Murphy JA (2000) Org Lett 2:3599
72. Zhou SZ, Bommezijn S, Murphy JA (2002) Org Lett 4:443
73. Rivkin A, Nagashina T, Curran DP (2003) Org Lett 5:419
74. Li F, Castle SL (2007) Org Lett 9:4033
75. Li F, Tartakoff SS, Castle SL (2009) J Org Chem 74:9082
76. Rigby JH, Qabar M (1991) J Am Chem Soc 113:8976
77. Rigby JH, Mateo ME (1996) Tetrahedron 52:10569
78. Schultz AG, Holoboski MA, Smyth MS (1993) J Am Chem Soc 115:7904
79. Schultz AG, Holoboski MA, Smyth MS (1996) J Am Chem Soc 118:6210
80. Rigby JH, Qabar MN (1993) J Org Chem 58:4473
81. Taniguchi T, Ishita A, Uchiyama M, Tamura O, Muraoka O, Tanabe G, Ishibashi H (2005) J Org Chem 70:1922
82. Taniguchi T, Iwasaki K, Uchiyama M, Tamura O, Ishibashi H (2005) Org Lett 7:4389
83. Tamura O, Yanagimachi T, Kobayashi T, Ishibashi H (2001) Org Lett 3:2427
84. Tamura O, Yanagimachi T, Ishibashi H (2003) Tetrahedron Asymmetry 14:3033
85. Kato I, Higashimoto M, Tamura O, Ishibashi H (2003) J Org Chem 68:7983
86. Orito K, Satoh Y, Nishizawa H, Harada R, Tokuda M (2000) Org Lett 2:2535
87. Nanni D (2001) In: Renaud P, Sibi MP (eds) Radicals in organic synthesis, 2nd edn. Wiley-VCH, Weinheim
88. Servais A, Azzouz M, Lopes D, Courillon C, Malacria M(2007) Angew Chem Int Ed 46:576
89. Kochi JK (1955) J Am Chem Soc 77:5090
90. Kochi JK (1955) J Am Chem Soc 77:5274
91. Rondestvedt CS (1976) Org React 24:225
92. Heinrich MR (2009), Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts, Chem Eur J 15:820, Copyright Wiley-VCH Verlag GmbH & Co. KGaA. Schemes 11, 13 and 16 reproduced with permission
93. Mastrorilli P, Nobile CF, Taccardi N (2006) Tetrahedron Lett 47:4759
94. Obushak ND, Matiichuk VS, Matyak RL (2003) Heterocycl Compd 39:878
95. Molinaro C, Mowat J, Gosselin F, O'Shea PD, Marcoux JF, Angelaud R, Davies IW (2007) J Org Chem 72:1856
96. Adel IA, Salami BA, Levisalles J, Rudler H (1976) Bull Soc Chim Fr 934
97. Citterio A, Minisci F, Albinati A, Bruckner S (1980) Tetrahedron Lett 21:2909
98. Citterio A, Ramperti M, Vismara E (1981) J Heterocycl Chem 18:763
99. Citterio A, Minisci F, Vismara E (1982) J Org Chem 47:81
100. Heinrich MR, Blank O, Wolfel S (2006) Org Lett 8:3323
101. Heinrich MR, Blank O, Wetzel A (2007) J Org Chem 72:476
102. Blank O, Wetzel A, Ullrich D, Heinrich MR (2008) Eur J Org Chem 18:3179
103. Heinrich MR, Blank O, Wetzel A (2006) Synlett 19:3352
104. Ganushchak NI, Grishchuk BD, Dombrovskii AV (1973) J Org Chem USSR 9:1030
105. Grishchuk BD, Gorbovoi PM, Ganuschak NI, Dombrovskii AV (1994) Russ Chem Rev 63:257
106. Heinrich MR, Kirschstein M (2006) Tetrahedron Lett 47:2115
107. Beckwith ALJ, Bowry VW, Ingold KU (1992) J Am Chem Soc 114:4983
108. Heinrich MR, Wetzel A, Kirschstein M (2007) Org Lett 9:3833
109. Grishchuk BD, Gorbovoi PM, Kudrik EY, Ganuschak NI, Kaspruk BI (1997) Russ J Gen Chem 67:362
110. Grishchuk BD, Kudrik EY, Gorbovoi PM, Ganushchak NI, Avrashkova TV (1997) Russ J Gen Chem 67:1556
111. Gorbovoi PM, Kudrik EY, Grishchuk BD (1998) Russ J Gen Chem 68:1132
112. Grishchuk BD, Kudrik EY, Gorbovoi PM, Ganushchak NI (1996) Russ J Gen Chem 66:1482
113. Tournier L, Zard SZ (2005) Tetrahedron Lett 46:971
114. Gorbovoi PM, Tulaidan GN, Grishchuk BD (2008) Russ J Gen Chem 78:133
115. Grishchuk BD, Baranovskii VS, Simchak RV, Tulaidan GN, Gorbovoi PM (2006) Russ J Gen Chem 76:936
116. Heinrich MR, Blank O, Ullrich D, Kirschstein M (2007) J Org Chem 72:9609
117. Benati L, Leardini R, Minozzi M, Nanni D, Spagnolo P, Zanardi G (2000) J Org Chem 65:8669
118. Benati L, Calestani G, Leardini R, Minozzi M, Nanni D, Spagnolo P, Strazzari S, Zanardi G (2003) J Org Chem 68:3454
119. Wassmundt FW, Kiesman WF (1995) J Org Chem 60:196
120. Ohno H, Iwasaki H, Eguchi T, Tanaka T (2004) Chem Commun 19:2228
121. Narasimhan NS, Aidhen IS (1988) Tetrahedron Lett 29:2987
122. Orito K, Uchiito S, Satoh Y, Tatsuzawa T, Harada R, Tokuda M (2000) Org Lett 2:307 and references cited therein
123. Rossi RA (2005) Synthetic organic photochemistry, 2nd edn. Marcel Dekker, New York
124. Rossi RA, Pierini AB, Peñéñory AB (2003) Chem Rev 103:71
125. Barolo SM, Teng X, Cuny GD, Rossi RA (2006) J Org Chem 71:8493
126. Donnelly S, Grimshaw J, Trocha-Grimshaw J (1994) J Chem Soc Chem Commun 18:2171 and references cited therein
127. Harrowven DC, Nunn MIT, Fenwick DR (2002) Tetrahedron Lett 43:7345
128. Harrowven DC, Guy IL, Nanson L (2006) Angew Chem Int Ed 45:2242
129. Moorthy JN, Samanta S (2007) J Org Chem 72:9786
130. Da Mata MLEN, Motherwell WB, Ujjainwalla F (1997) Tetrahedron Lett 38:137
131. Alcaide B, Rodriguez-Vicente A (1998) Tetrahedron Lett 39:6589
132. Clive DLJ, Kang S (2000) Tetrahedron Lett 41:1315
133. Studer A, Bossart M, Vasella T (2000) Org Lett 2:985
134. Hey DH, Jones GH, Perkins MJ (1971) J Chem Soc C 116
135. De Turiso FGL, Curran DP (2005) Org Lett 7:151
136. Lanza T, Leardini R, Minozzi M, Nanni D, Spagnolo P, Zanardi G (2008) Angew Chem Int Ed 47:9439
137. Ho TCT, Jones K (1997) Tetrahedron 53:8287
138. Harrowven DC, Sutton BJ, Coulton S (2002) Tetrahedron 58:3387
139. Flanagan SR, Harrowven DC, Bradley M (2003) Tetrahedron Lett 44:1795
140. Ganguly AK, Wang CH, Chan TM, Ing YH, Buevich AV (2004) Tetrahedron Lett 45:883
141. Allin SM, Bowman WR, Elsegood MRJ, McKee V, Karim R, Rahman SS (2005) Tetrahedron 61:2689
142. Harrowven DC, Sutton BJ, Coulton S (2003) Org Biomol Chem 1:4047
143. Escolano C, Jones K (2002) Tetrahedron 58:1453
144. Harrowven DC, Woodcock T, Howes PD (2005) Angew Chem Int Ed 44:3899
145. Beadle JR, Korzeniowski SH, Rosenberg DE, Garcia-Slanga BJ, Gokel GW (1984) J Org Chem 49:1594
146. Demir AS, Reis O ̈ , Emrullahoglu M (2003) J Org Chem 68:578
147. Demir AS, Reis O ̈ , Ö zgul-Karaaslan (2001) J Chem Soc Perkin Trans 1 3042
148. Curran DP, Keller AI (2006) J Am Chem Soc 128:13706
149. Chatgilialoglu C (2008) Chem Eur J 14:2310
150. Androsov DA, Neckers DC (2007) J Org Chem 72:1148
151. Kosynkin D, Bockman TM, Kochi JK (1997) J Am Chem Soc 119:4846
152. Petrillo G, Novi M, Dell'Erba C, Tavan C (1991) Tetrahedron 47:9297
153. Wetzel A, Ehrhardt V, Heinrich MR (2008) Angew Chem 120:9270;
154. (2008) Angew Chem Int Ed 47:9130
155. Wetzel A, Pratsch G, Kolb R, Heinrich MR (2010) Chem Eur J 16:2547
156. Crich D, Patel M (2006) Tetrahedron 62:7824
157. Martinez-Barrasa V, De Viedma AG, Burgos C, Alvarez-Builla J (2000) Org Lett 2:3933
158. Núnez A, Sánchez A, Burgos C, Alvarez-Builla J (2004) Tetrahedron 60:6217
159. Ryu I, Kreimerman S, Araki F, Nishitani S, Oderaotoshi Y, Minakata S, Komatsu M (2002) J Am Chem Soc 124:3812
160. Manolikakes G, Knochel P (2009) Angew Chem Int Ed 48:205
161. Ford L, Jahn U (2009) Angew Chem Int Ed 48:6386
162. Kobayashi T, Ohmiya H, Yorimitsu H, Oshima KJ (2008) J Am Chem Soc 130:11276
163. Gansauer A, Fan CA, Piestert FJ (2008) J Am Chem Soc 130:6916