Abstract
The development of transition-metal-free arylation procedures represents a key goal
in modern organic synthesis. A green arylation can be obtained by having recourse
to light as a ‘clean’ reagent in place of toxic metals. In particular, a new method
based upon the photoheterolytic fragmentation of substituted aryl halides or esters,
with the formation of aryl cations has recently emerged. The peculiar reactivity of
these cations with carbon nucleophiles allows several straightforward photo-arylations,
which compare favorably with other thermal or photochemical metal-free analogues.
1 Introduction
2 Aryl Cation Chemistry
3 Metal-Free Formation of Aryl-Carbon Bonds
3.1 Formation of Aryl-Alkyl Bonds
3.1.1 Arylation of Carbonyl Compounds
3.1.2 Formation of Aryl-Allyl Bonds
3.1.3 Formation of Other Aryl-Alkyl Bonds
3.2 Formation of Aryl-Vinyl Bonds
3.3 Formation of Aryl-Alkynyl Bonds
3.4 Formation of Aryl-Aryl Bonds
3.5 Cyanation
4 Conclusions
Key words
arylation - aryl cation - aromatic substitution - metal-free procedures - photochemistry
References
1a </A>
Transition Metals for Organic Synthesis
Beller M.
Bolm C.
Wiley-VCH;
Weinheim:
1998.
1b </A>
Tsuji J. In Palladium Reagents and Catalysts
John Wiley & Sons;
Chichester:
2004.
1c </A>
Tsuji J. In Transition Metal Reagents and Catalysts
John Wiley & Sons;
Chichester:
2000.
<A NAME="RA47707ST-2">2 </A>
Beller M.
Zapf A.
Maegerlein W.
Chem. Eng. Technol.
2001,
24:
575
3a </A>
Kielhorn J.
Melber C.
Keller D.
Mangelsdorf I.
Int. J. Hyg. Environ. Health
2002,
205:
417
3b </A>
Mehta R.
Templeton DM.
O’Brien PJ.
Chem.-Biol. Interact.
2006,
163:
77
3c </A>
Huang X.-P.
O’Brien PJ.
Templeton DM.
Chem.-Biol. Interact.
2006,
163:
68
4a </A>
Zhdankin VV.
Stang PJ.
Chem. Rev.
2002,
102:
2523
4b </A>
Studer A.
Bossart M. In Radicals in Organic Synthesis
Vol. 2:
Renaud P.
Sibi M.
Wiley-VCH;
Weinheim:
2001.
p.62-80
4c </A>
Nucleophilic Aromatic Substitutions, In Comprehensive Organic Synthesis
Vol. 4:
Trost BM.
Fleming I.
Pergamon Press;
Oxford:
1991.
Chap. 2.1-2.3.
p.423-515
5a </A>
Wenk HH.
Winkler M.
Sander W.
Angew. Chem. Int. Ed.
2003,
42:
502
5b </A>
Pellissier H.
Santelli M.
Tetrahedron
2003,
59:
701
5c </A>
Peña D.
Pérez D.
Guitián E.
Angew. Chem. Int. Ed.
2006,
45:
3579
6 </A>
Dichiarante, V.; Fagnoni, M.; Albini, A. Photochemical Arylation Reactions , In Modern Arylation Methods ; Ackermann, L., Ed.; Wiley-VCH: Weinheim, in preparation.
7a </A>
Stang PJ. In Dicoordinated Carbocations
Rappoport Z.
Stang PJ.
Wiley;
New York:
1997.
p.451
7b </A>
Hanack M.
Subramanian LR. In Houben-Weyl, Methoden der organischen Chemie
Vol. E19c:
Hanck M.
Thieme;
Stuttgart:
1990.
p.249
8a </A>
Lazzaroni S.
Dondi D.
Fagnoni M.
Albini A.
J. Org. Chem.
2008,
73:
206
8b </A>
Aschi M.
Harvey JN.
J. Chem. Soc., Perkin Trans. 2
1999,
1059
8c </A>
Laali KK.
Rasul G.
Prakash GKS.
Olah GA.
J. Org. Chem.
2002,
67:
2913
8d </A>
Slegt M.
Overkleeft HS.
Lodder G.
Eur. J. Org. Chem.
2007,
5364
8e </A>
Dichiarante V.
Fagnoni M.
Albini A.
J. Org. Chem.
2008,
73:
1282
9a </A>
Himeshima Y.
Kobayashi H.
Sonoda T.
J. Am. Chem. Soc.
1985,
107:
5286
9b </A>
Apeloig Y.
Arad D.
J. Am. Chem. Soc.
1985,
107:
5285
9c </A>
Subramanian LR.
Hanack M.
Chang LW.
Imhoff MA.
Schleyer PvR.
Effenberger F.
Kurtz W.
Stang PJ.
Dueber TE.
J. Org. Chem.
1976,
41:
4099
9d </A>
Laali K.
Szele I.
Yoshida K.
Helv. Chim. Acta
1983,
66:
1710
10a </A>
Holweger W.
Hanack M.
Chem. Ber.
1984,
117:
3004
10b </A>
Bleckmann W.
Hanack M.
Chem. Ber.
1984,
117:
3021
10c </A>
Hanack M.
Rieth R.
Chem. Ber.
1987,
120:
1659
11a </A>
Romsted LS.
Zhang J.
Zhang L.
J. Am. Chem. Soc.
1998,
120:
10046
11b </A>
Chauduri A.
Loughlin JA.
Romsted LS.
Yao J.
J. Am. Chem. Soc.
1993,
115:
8351
11c </A>
Swain CG.
Sheats JE.
Harbison KG.
J. Am. Chem. Soc.
1975,
97:
783
11d </A>
Bergstrom RG.
Landells RGM.
Wahl GW.
Zollinger H.
J. Am. Chem. Soc.
1976,
98:
3301
<A NAME="RA47707ST-12">12 </A>
Dichiarante V.
Salvaneschi A.
Protti S.
Dondi D.
Fagnoni M.
Albini A.
J. Am. Chem. Soc.
2007,
129:
15919
<A NAME="RA47707ST-13">13 </A>
Dichiarante V.
Dondi D.
Protti S.
Fagnoni M.
Albini A.
J. Am. Chem. Soc.
2007,
129:
5605
<A NAME="RA47707ST-14">14 </A>
Zollinger H.
Diazochemistry I
VCH;
New York:
1995.
<A NAME="RA47707ST-15">15 </A>
Steenken S.
Askokkuna M.
Maruthamuthu P.
McClelland RA.
J. Am. Chem. Soc.
1998,
120:
11925
<A NAME="RA47707ST-16">16 </A>
Gasper SM.
Devadoss C.
Schuster GB.
J. Am. Chem. Soc.
1995,
117:
5206
17a </A>
Fasani E.
Mella M.
Caccia D.
Tassi S.
Fagnoni M.
Albini A.
Chem. Commun.
1997,
1329
17b </A>
Albini A.
Monti S.
Chem. Soc. Rev.
2003,
32:
238
18a </A>
Fagnoni M.
Albini A.
Acc. Chem. Res.
2005,
38:
713
18b </A>
Fagnoni M.
Lett. Org. Chem.
2006,
3:
253
19a </A>
Milanesi S.
Fagnoni M.
Albini A.
J. Org. Chem.
2005,
70:
603
19b </A>
Milanesi S.
Fagnoni M.
Albini A.
Chem. Commun.
2003,
216
<A NAME="RA47707ST-20">20 </A>
Olah GA.
Krishnamurti R.
Prakash GK.
Friedel-Crafts Alkylation , In Comprehensive Organic Synthesis
Vol. 3:
Trost BM.
Fleming I.
Pergamon Press;
Oxford:
1991.
p.293
<A NAME="RA47707ST-21">21 </A>
Culkin DA.
Hartwig JF.
Acc. Chem. Res.
2003,
36:
234
22a </A>
Snow RJ.
Butz T.
Hammach A.
Kapadia S.
Morwick TM.
Prokopowicz AS.
Takahashi H.
Tan JD.
Tschantza MAM.
Wangb X.-J.
Tetrahedron Lett.
2002,
43:
7553
22b </A>
Selvakumar N.
Yadi Reddy B.
Azhagan AM.
Khera MK.
Babu JM.
Iqbal J.
Tetrahedron Lett.
2003,
44:
7065
22c </A>
Ueno M.
Yonemoto M.
Hashimoto M.
Wheatley AEH.
Naka H.
Kondo Y.
Chem. Commun.
2007,
2264
22d </A>
Selvakumar N.
Yadi Reddy B.
Kumar GS.
Iqbal J.
Tetrahedron Lett.
2001,
42:
8395
22e </A>
Bella M.
Koppelgaard S.
Jørgensen KA.
J. Am. Chem. Soc.
2005,
127:
3670
22f </A>
Koppelgaard S.
Bella M.
Jørgensen KA.
J. Org. Chem.
2006,
71:
4980
23a </A>
Shen HC.
Ding F.-X.
Colletti SL.
Org. Lett.
2006,
8:
1447
23b </A>
Klaspars A.
Waldman JH.
Campos KR.
Jensen MS.
McLaughlin M.
Chung JYL.
Cvetovich RJ.
Chen C.
J. Org. Chem.
2005,
70:
10186
23c </A>
Lawrence NJ.
Davies CA.
Gray M.
Org. Lett.
2004,
6:
4957
24a </A>
Rossi RA.
Peñéñory AB.
Curr. Org. Synth.
2006,
3:
121
24b </A>
Rossi RA.
Photoinduced Aromatic Nucleophilic Substitution Reactions In Molecular and Supramolecular Photochemistry
Vol. 12:
Griesbeck AG.
Mattay J.
Dekker;
New York:
2005.
p.495
<A NAME="RA47707ST-25">25 </A>
Guastavino JF.
Barolo SM.
Rossi RA.
Eur. J. Org. Chem.
2006,
3898
<A NAME="RA47707ST-26">26 </A>
Molinaro C.
Mowat J.
Gosselin F.
O’Shea PD.
Marcoux J.-F.
Angelaud R.
Davies IW.
J. Org. Chem.
2007,
72:
1856
27a </A>
Crary JW.
Quayle OR.
Lester CT.
J. Am. Chem. Soc.
1956,
78:
5584
27b </A>
Sakakura T.
Hara M.
Tanaka M.
J. Chem. Soc., Perkin Trans. 1
1994,
289
<A NAME="RA47707ST-28">28 </A>
Fraboni A.
Fagnoni M.
Albini A.
J. Org. Chem.
2003,
68:
4886
<A NAME="RA47707ST-29">29 </A>
Parmar VS.
Jain SC.
Bisht KP.
Jain R.
Taneja P.
Jha A.
Tyagi OD.
Prasad AK.
Wengel J.
Olsen CE.
Boll PM.
Phytochemistry
1997,
46:
597
<A NAME="RA47707ST-30">30 </A>
Ek F.
Axelsson O.
Wistrand L.-G.
Frejd T.
J. Org. Chem.
2002,
67:
6376
<A NAME="RA47707ST-31">31 </A>
Nakanishi K.
Mizuno K.
Otsuji Y.
Bull. Chem. Soc. Jpn.
1993,
66:
2371
<A NAME="RA47707ST-32">32 </A>
Protti S.
Fagnoni M.
Albini A.
Org. Biomol. Chem.
2005,
3:
2868
<A NAME="RA47707ST-33">33 </A>
De Carolis M.
Protti S.
Fagnoni M.
Albini A.
Angew. Chem. Int. Ed.
2005,
44:
1232
<A NAME="RA47707ST-34">34 </A>
Manet I.
Monti S.
Fagnoni M.
Protti S.
Albini A.
Chem. Eur. J.
2005,
11:
140
<A NAME="RA47707ST-35">35 </A>
Mella M.
Coppo P.
Guizzardi B.
Fagnoni M.
Freccero M.
Albini A.
J. Org. Chem.
2001,
66:
6344
<A NAME="RA47707ST-36">36 </A>
Fagnoni M.
Mella M.
Albini A.
Org. Lett.
1999,
1:
1299
<A NAME="RA47707ST-37">37 </A>
Dichiarante V.
Betti C.
Fagnoni M.
Maia A.
Landini D.
Albini A.
Chem. Eur. J.
2007,
13:
1834
<A NAME="RA47707ST-38">38 </A>
Lazzaroni S.
Dondi D.
Fagnoni M.
Albini A.
Eur. J. Org. Chem.
2007,
4360
<A NAME="RA47707ST-39">39 </A>
Protti S.
Fagnoni M.
Mella M.
Albini A.
J. Org. Chem.
2004,
69:
3465
<A NAME="RA47707ST-40">40 </A>
Guizzardi B.
Mella M.
Fagnoni M.
Albini A.
Chem. Eur. J.
2003,
9:
1549
<A NAME="RA47707ST-41">41 </A>
Dichiarante V.
Fagnoni M.
Mella M.
Albini A.
Chem. Eur. J.
2006,
12:
3905
<A NAME="RA47707ST-42">42 </A>
Zhang W.
Curr. Org. Chem.
2004,
8:
757
<A NAME="RA47707ST-43">43 </A>
Menes-Arzate M.
Martinez R.
Cruz-Almanza R.
Muchowski JM.
Osornio YM.
Miranda LD.
J. Org. Chem.
2004,
69:
4001
<A NAME="RA47707ST-44">44 </A>
Zhang W.
Pugh G.
Tetrahedron
2003,
59:
3009
<A NAME="RA47707ST-45">45 </A>
Kojima T.
Ohishi T.
Yamamoto I.
Matsuoka T.
Kotsuki H.
Tetrahedron Lett.
2001,
42:
1709
<A NAME="RA47707ST-46">46 </A>
Yoshida H.
Morishita T.
Fukushima H.
Ohshita J.
Kunai A.
Org. Lett.
2007,
9:
3367
<A NAME="RA47707ST-47">47 </A>
Sparks SM.
Chen C.-L.
Martin SF.
Tetrahedron
2007,
63:
8619
<A NAME="RA47707ST-48">48 </A>
Protti S.
Fagnoni M.
Albini A.
J. Am. Chem. Soc.
2006,
128:
10670
<A NAME="RA47707ST-49">49 </A>
Protti, S.; Dondi, D.; Fagnoni, M.; Albini, A. Eur. J. Org. Chem. , accepted for publication.
<A NAME="RA47707ST-50">50 </A>
Wolfe JP.
Eur. J. Org. Chem.
2007,
571
<A NAME="RA47707ST-51">51 </A>
Beletskaya IP.
Cheprakov AV.
Chem. Rev.
2000,
100:
3009 ; and references cited therein
<A NAME="RA47707ST-52">52 </A>
Knowles JP.
Whiting A.
Org. Biomol. Chem.
2007,
5:
31
<A NAME="RA47707ST-53">53 </A>
Choi DS.
Kim JH.
Shin US.
Deshmukh RR.
Song CE.
Chem. Commun.
2007,
3482 ; and references cited therein
<A NAME="RA47707ST-54">54 </A>
Arvela RK.
Leadbeater NE.
Sangi MS.
Williams VA.
Granados P.
Singer RD.
J. Org. Chem.
2005,
70:
161
<A NAME="RA47707ST-55">55 </A>
Tykwinski RR.
Angew. Chem. Int. Ed.
2003,
42:
1566
<A NAME="RA47707ST-56">56 </A>
Doucet H.
Hierso J.-C.
Angew. Chem. Int. Ed.
2007,
46:
834
<A NAME="RA47707ST-57">57 </A>
Appukkuttan P.
Dehaen W.
Van der Eycken E.
Eur. J. Org. Chem.
2003,
4713
<A NAME="RA47707ST-58">58 </A>
Leadbeater NE.
Marco M.
Tominack BJ.
Org. Lett.
2003,
5:
3919
<A NAME="RA47707ST-59">59 </A>
DeRoy PL.
Surprenant S.
Bertrand-Laperle M.
Yoakim C.
Org. Lett.
2007,
9:
2741
<A NAME="RA47707ST-60">60 </A>
Protti S.
Fagnoni M.
Albini A.
Angew. Chem. Int. Ed.
2005,
44:
5675
<A NAME="RA47707ST-61">61 </A>
Okuyama T.
Acc. Chem. Res.
2002,
35:
12
<A NAME="RA47707ST-62">62 </A>
Hassan J.
Sevignon M.
Gozzi C.
Schulz E.
Lemaire M.
Chem. Rev.
2002,
102:
1359
63a </A>
Campeau L.-C.
Fagnou K.
Chem. Commun.
2006,
1253
63b </A>
Alberico D.
Scott ME.
Lautens M.
Chem. Rev.
2007,
107:
174
<A NAME="RA47707ST-64">64 </A>
Harrowven DC.
Sutton BJ.
Coulton S.
Org. Biomol. Chem.
2003,
1:
4047
<A NAME="RA47707ST-65">65 </A>
Norman DPG.
Bunnell AE.
Stabler SR.
Flippin LA.
J. Org. Chem.
1999,
64:
9301
<A NAME="RA47707ST-66">66 </A>
Kehlbeck JD.
Dimise EJ.
Sparks SM.
Ferrara S.
Tanski JM.
Anderson CM.
Synthesis
2007,
1979
<A NAME="RA47707ST-67">67 </A>
Beckwith ALJ.
Bowry VW.
Bowman WR.
Mann E.
Parr J.
Storey JMD.
Angew. Chem. Int. Ed.
2004,
43:
95
<A NAME="RA47707ST-68">68 </A>
Curran DP.
Keller AI.
J. Am. Chem. Soc.
2006,
128:
13706
<A NAME="RA47707ST-69">69 </A>
Ho T.-I.
Ku C.-K.
Liu RSH.
Tetrahedron Lett.
2001,
42:
715
<A NAME="RA47707ST-70">70 </A>
Dichiarante V.
Fagnoni M.
Albini A.
Angew. Chem. Int. Ed.
2007,
46:
6495
<A NAME="RA47707ST-71">71 </A>
Guizzardi B.
Mella M.
Fagnoni M.
Albini A.
Tetrahedron
2000,
56:
9383
<A NAME="RA47707ST-72">72 </A>
Sundermeier M.
Zapf A.
Beller M.
Eur. J. Inorg. Chem.
2003,
3513
<A NAME="RA47707ST-73">73 </A>
Sun H.
DiMagno SG.
J. Am. Chem. Soc.
2005,
127:
2050
<A NAME="RA47707ST-74">74 </A>
Gallardo I.
Guirado G.
Marquet J.
J. Org. Chem.
2002,
67:
2548
<A NAME="RA47707ST-75">75 </A>
Gallardo I.
Guirado G.
Marquet J.
Chem. Eur. J.
2001,
7:
1759
<A NAME="RA47707ST-76">76 </A>
Fagnoni M.
Albini A.
Photonucleophilic Substitution Reactions , In Molecular and Supramolecular Photochemistry
Vol. 14:
Ramamurthy V.
Schanze K.
Dekker;
New York:
2006.
p.131
<A NAME="RA47707ST-77">77 </A>
Kitagawa F.
Murase M.
Kitamura N.
J. Org. Chem.
2002,
67:
2524
<A NAME="RA47707ST-78">78 </A>
Dichiarante V.
Fagnoni M.
Albini A.
Chem. Commun.
2006,
3001
