Abstract
This review with 206 references covers the literature published until March 2004 on
the development and applications of new efficient catalyst systems for the Suzuki
palladium-catalysed cross-coupling reaction of organoboron compounds with organic
electrophiles. Where possible, the relative advantages of the new catalyst systems
in this synthetically very important carbon-carbon bond forming reaction have been
compared.
1 Introduction
2 Palladacycle Complexes as Catalyst Precursors
3 Catalyst Systems Composed of Pd(0) or Pd(II) Derivatives and Electron-Rich and/or
Bulky Phosphine Ligands
4 Catalyst Systems Composed of Pd(0) or Pd(II) Derivatives and N -Heterocyclic Carbene Ligands
5 Water-Soluble Catalyst Precursors
6 Ligandless Catalyst Precursors
7 Other Novel Pd Catalyst Precursors
8 Conclusions
Key words
palladium - complexes - boron - catalysis - cross-coupling
References
<A NAME="RE11404SS-1">1 </A>
Smith GB.
Dezeny GC.
Hughes DL.
King AO.
Verhoeven TR.
J. Org. Chem.
1994,
59:
8151
<A NAME="RE11404SS-2">2 </A>
Ennis DS.
McManus J.
Wood-Kaczmar W.
Richardson J.
Smith GE.
Carstairs A.
Org. Process Res. Dev.
1999,
3:
248
<A NAME="RE11404SS-3">3 </A>
Jacks TE.
Belmont DT.
Briggs CA.
Horne NM.
Kanter GD.
Karrick GL.
Krikke JJ.
McCabe RJ.
Mustakis JG.
Nanninga TN.
Risedorph GS.
Seamans RE.
Skeenan RE.
Winkle DD.
Zennie TM.
Org. Process Res. Dev.
2004,
8:
201
<A NAME="RE11404SS-4">4 </A>
Miyaura N.
Suzuki A.
Chem. Rev.
1995,
95:
2457
<A NAME="RE11404SS-5">5 </A>
Suzuki A. In Metal-Catalyzed Cross-Coupling Reactions
Diederich F.
Stang PJ.
Wiley-VCH;
Weinheim:
1998.
p.49-97
<A NAME="RE11404SS-6">6 </A>
Suzuki A.
Pure Appl. Chem.
1994,
66:
213
<A NAME="RE11404SS-7">7 </A>
Stanforth SP.
Tetrahedron
1998,
54:
263
<A NAME="RE11404SS-8">8 </A>
Suzuki A.
J. Organomet. Chem.
1999,
576:
147
<A NAME="RE11404SS-9">9 </A>
Suzuki A. In Organoboranes for Syntheses. ACS Symposium Series 783
Ramachandran PV.
Brown HC.
American Chemical Society;
Washington DC:
2001.
p.80-93
<A NAME="RE11404SS-10">10 </A>
Kotha S.
Lahiri K.
Kashinath D.
Tetrahedron
2002,
58:
9633
<A NAME="RE11404SS-11">11 </A>
Miyaura N.
Top. Curr. Chem.
2002,
219:
11
<A NAME="RE11404SS-12">12 </A>
Lloyd-Williams P.
Giralt E.
Chem. Soc. Rev.
2001,
30:
145
<A NAME="RE11404SS-13">13 </A>
Littke AF.
Fu GC.
Angew. Chem. Int. Ed.
2002,
41:
4176
<A NAME="RE11404SS-14">14 </A>
Herrmann WA.
Böhm VPW.
Reisinger C.-P.
J. Organomet. Chem.
1999,
576:
23
<A NAME="RE11404SS-15">15 </A>
Dupont J.
Pfeffer M.
Spencer J.
Eur. J. Inorg. Chem.
2001,
1917
<A NAME="RE11404SS-16">16 </A>
Shaw BL.
New J. Chem.
1998,
77
<A NAME="RE11404SS-17">17 </A>
Beller M.
Fischer H.
Herrmann WA.
Öfele K.
Brossmer C.
Angew. Chem., Int. Ed. Engl.
1995,
34:
1848
<A NAME="RE11404SS-18">18 </A>
Darses S.
Michaud G.
Genêt J.-P.
Eur. J. Org. Chem.
1999,
1875
<A NAME="RE11404SS-19">19 </A>
Albisson DA.
Bedford RB.
Lawrence SE.
Scully PN.
Chem. Commun.
1998,
2095
<A NAME="RE11404SS-20">20 </A>
Bedford RB.
Hazelwood (née Welch) SL.
Limmert ME.
Albisson DA.
Draper SM.
Scully PN.
Coles SJ.
Hursthouse MB.
Chem.-Eur. J.
2003,
9:
3216
<A NAME="RE11404SS-21">21 </A>
Weissman H.
Milstein D.
Chem. Commun.
1999,
1901
<A NAME="RE11404SS-22">22 </A>
Alonso DA.
Nájera C.
Pacheco MC.
Org. Lett.
2000,
2:
1823
<A NAME="RE11404SS-23">23 </A>
Alonso DA.
Nájera C.
Pacheco MC.
J. Org. Chem.
2002,
67:
5588
<A NAME="RE11404SS-24">24 </A>
Botella L.
Nájera C.
Angew. Chem. Int. Ed.
2002,
41:
179
<A NAME="RE11404SS-25">25 </A>
Botella L.
Nájera C.
J. Organomet. Chem.
2002,
663:
46
<A NAME="RE11404SS-26">26 </A>
Alonso DA.
Botella L.
Nájera C.
Pacheco MC.
Synthesis
2004,
1713
<A NAME="RE11404SS-27">27 </A>
Bedford RB.
Draper SM.
Scully PN.
Welch SL.
New J. Chem.
2000,
24:
745
<A NAME="RE11404SS-28">28 </A>
Bedford RB.
Welch S.
Chem. Commun.
2001,
129
<A NAME="RE11404SS-29">29 </A>
Zim D.
Gruber AS.
Ebeling G.
Dupont J.
Monteiro AL.
Org. Lett.
2000,
2:
2881
<A NAME="RE11404SS-30">30 </A>
Albisson DA.
Bedford RB.
Scully PN.
Tetrahedron Lett.
1998,
39:
9793
<A NAME="RE11404SS-31">31 </A>
Bedford RB.
Cazin CSJ.
Chem. Commun.
2001,
1540
<A NAME="RE11404SS-32">32 </A>
Bedford RB.
Cazin CSJ.
Coles SJ.
Gelbrich T.
Hursthouse MB.
Scordia VJM.
J. Chem. Soc., Dalton Trans.
2003,
3350
<A NAME="RE11404SS-33">33 </A>
Bedford RB.
Cazin CSJ.
Coles SJ.
Gelbrich T.
Horton PN.
Hursthouse MB.
Light ME.
Organometallics
2003,
22:
987
<A NAME="RE11404SS-34">34 </A>
Bedford RB.
Cazin CSJ.
Hursthouse MB.
Light ME.
Pike KJ.
Wimperis S.
J. Organomet. Chem.
2001,
633:
173
<A NAME="RE11404SS-35">35 </A>
Gibson S.
Foster DF.
Eastham GR.
Tooze RP.
Cole-Hamilton DJ.
Chem. Commun.
2001,
779
<A NAME="RE11404SS-36">36 </A>
Schnyder A.
Indolese AF.
Studer M.
Blaser H.-U.
Angew. Chem. Int. Ed.
2002,
41:
3668
<A NAME="RE11404SS-37">37 </A>
Bellina F.
Anselmi C.
Martina F.
Rossi R.
Eur. J. Org. Chem.
2003,
68:
2290
<A NAME="RE11404SS-38">38 </A>
Bedford RB.
Cazin CSJ.
Hazelwood (née Welch) SL.
Angew. Chem. Int. Ed.
2002,
41:
4120
<A NAME="RE11404SS-39">39 </A>
Bedford RB.
Hazelwood (née Welch) SL.
Limmert ME.
Chem. Commun.
2002,
2610
<A NAME="RE11404SS-40">40 </A>
Roca FX.
Richards CJ.
Chem. Commun.
2003,
3002
<A NAME="RE11404SS-41">41 </A>
Thakur VV.
Kumar NSCR.
Sudalai A.
Tetrahedron Lett.
2004,
45:
2915
<A NAME="RE11404SS-42">42 </A>
Bedford RB.
Chem. Commun.
2003,
1787
<A NAME="RE11404SS-43">43 </A>
Li JJ.
Gribble GW.
Palladium in Heterocyclic Chemistry: A guide for the synthetic chemist
Elsevier;
Oxford:
2000.
44a </A>
Uemura M.
Nishimura H.
Kamikawa K.
Nakayama K.
Hayashi Y.
Tetrahedron Lett.
1994,
35:
1909
44b </A>
Uemura M.
Nishimura H.
Hayashi T.
J. Organomet. Chem.
1994,
473:
129
44c </A>
See ref. 17.
44d </A>
Mitchell MB.
Wallbank PJ.
Tetrahedron Lett.
1991,
32:
2273
<A NAME="RE11404SS-45">45 </A>
Shen W.
Tetrahedron Lett.
1997,
38:
5575
<A NAME="RE11404SS-46">46 </A>
Firooznia F.
Gude C.
Chan K.
Satoh Y.
Tetrahedron Lett.
1998,
39:
3985
<A NAME="RE11404SS-47">47 </A>
McKenna JM.
Moliterni J.
Qiao Y.
Tetrahedron Lett.
2001,
42:
5797
<A NAME="RE11404SS-48">48 </A>
Minutolo F.
Bertini S.
Papi C.
Carlson KE.
Katzenellenbogen JA.
Macchia M.
J. Med. Chem.
2001,
44:
4288
<A NAME="RE11404SS-49">49 </A>
McClure MS.
Glover B.
McSorley E.
Millar A.
Osterhout MH.
Roschangar F.
Org. Lett.
2001,
3:
1677
<A NAME="RE11404SS-50">50 </A>
Monteith MJ. inventors; WO 9816486.
<A NAME="RE11404SS-51">51 </A>
Monteith MJ.
Spec. Chem.
1998,
18:
436
<A NAME="RE11404SS-52">52 </A>
Littke AF.
Fu GC.
Angew. Chem. Int. Ed.
1998,
37:
3387
<A NAME="RE11404SS-53">53 </A>
Littke AF.
Dai C.
Fu GC.
J. Am. Chem. Soc.
2000,
122:
4020
<A NAME="RE11404SS-54">54 </A>
Kirchhoff JH.
Dai C.
Fu GC.
Angew. Chem. Int. Ed.
2002,
41:
1945
<A NAME="RE11404SS-55">55 </A>
Allegretti M.
Arcadi A.
Marinelli F.
Nicolini L.
Synlett
2001,
609
<A NAME="RE11404SS-56">56 </A>
Brill WK.-D.
Riva-Toniolo C.
Müller S.
Synlett
2001,
1097
<A NAME="RE11404SS-57">57 </A>
Sutton AE.
Clardy J.
Tetrahedron Lett.
2001,
42:
547
<A NAME="RE11404SS-58">58 </A>
Mello JV.
Finney NS.
Org. Lett.
2001,
3:
4263
<A NAME="RE11404SS-59">59 </A>
Zou G.
Falck JR.
Tetrahedron Lett.
2001,
42:
5817
<A NAME="RE11404SS-60">60 </A>
Bellina, F.; Rossi, R. unpublished results.
<A NAME="RE11404SS-61">61 </A>
Bellina F.
Anselmi C.
Rossi R.
Tetrahedron Lett.
2002,
43:
2023
<A NAME="RE11404SS-62">62 </A>
Rossi, R.; Bellina, F. unpublished results.
<A NAME="RE11404SS-63">63 </A>
Netherton MR.
Fu GC.
Org. Lett.
2001,
3:
4295
<A NAME="RE11404SS-64">64 </A>
Zhong Y.-L.
Lee J.
Reamer RA.
Askin D.
Org. Lett.
2004,
6:
929
<A NAME="RE11404SS-65">65 </A>
Kirchhoff JH.
Netherton MR.
Hills ID.
Fu GC.
J. Am. Chem. Soc.
2002,
124:
13662
<A NAME="RE11404SS-66">66 </A>
Zapf A.
Ehrentraut A.
Beller M.
Angew. Chem. Int. Ed.
2000,
39:
4153
<A NAME="RE11404SS-67">67 </A>
Stambuli JP.
Kuwano R.
Hartwig JF.
Angew. Chem. Int. Ed.
2002,
41:
4746
<A NAME="RE11404SS-68">68 </A>
Old DW.
Wolfe JP.
Buchwald SL.
J. Am. Chem. Soc.
1998,
120:
9722
<A NAME="RE11404SS-69">69 </A>
Wolfe JP.
Buchwald SL.
Angew. Chem. Int. Ed.
1999,
38:
2413
<A NAME="RE11404SS-70">70 </A>
Wolfe JP.
Singer RA.
Yang BH.
Buchwald SL.
J. Am. Chem. Soc.
1999,
121:
9550
<A NAME="RE11404SS-71">71 </A>
Yin J.
Buchwald SL.
J. Am. Chem. Soc.
2000,
122:
12051
<A NAME="RE11404SS-72">72 </A>
Yin J.
Rainka MP.
Zhang X.-X.
Buchwald SL.
J. Am. Chem. Soc.
2002,
124:
1162
<A NAME="RE11404SS-73">73 </A>
Nguyen HN.
Huang X.
Buchwald SL.
J. Am. Chem. Soc.
2003,
125:
11818
<A NAME="RE11404SS-74">74 </A>
Walker SD.
Barder TE.
Martinelli JR.
Buchwald SL.
Angew. Chem. Int. Ed.
2004,
43:
1871
<A NAME="RE11404SS-75">75 </A>
Dyer UC.
Shapland PD.
Tiffin PD.
Tetrahedron Lett.
2001,
42:
1765
<A NAME="RE11404SS-76">76 </A>
Tagata T.
Nishida M.
J. Org. Chem.
2003,
68:
9412
<A NAME="RE11404SS-77">77 </A>
Lakshman MK.
Hilmer JH.
Martin JQ.
Keeler JC.
Dinh YQV.
Ngassa FN.
Russon LM.
J. Am. Chem. Soc.
2001,
123:
7779
<A NAME="RE11404SS-78">78 </A>
Lakshman MK.
Thompson PF.
Nuqui MA.
Hilmer JH.
Sevova N.
Boggess B.
Org. Lett.
2002,
4:
1479
<A NAME="RE11404SS-79">79 </A>
Sugihara S.
Kuroda N.
Wada M.
Nakashima K.
Anal. Sci.
2001,
17 (Supplement I):
1261
<A NAME="RE11404SS-80">80 </A>
Kotharé MA.
Ohkanda J.
Lockman JW.
Qian Y.
Blaskovich MA.
Sebti SM.
Hamilton AD.
Tetrahedron
2000,
56:
9833
<A NAME="RE11404SS-81">81 </A>
Parrish CA.
Buchwald SL.
J. Org. Chem.
2001,
66:
3820
<A NAME="RE11404SS-82">82 </A>
Zapf A.
Jackstell R.
Rataboul F.
Riermeier T.
Monsees A.
Fuhrmann C.
Shaikh N.
Dingerdissen U.
Beller M.
Chem. Commun.
2004,
38
<A NAME="RE11404SS-83">83 </A>
Pickett TE.
Richards CJ.
Tetrahedron Lett.
2001,
42:
3767
<A NAME="RE11404SS-84">84 </A>
Pickett TE.
Roca FX.
Richards CJ.
J. Org. Chem.
2003,
68:
2592
<A NAME="RE11404SS-85">85 </A>
Liu S.-Y.
Choi MJ.
Fu GC.
Chem. Commun.
2001,
2408
<A NAME="RE11404SS-86">86 </A>
Kataoka N.
Shelby Q.
Stambuli JP.
Hartwig JF.
J. Org. Chem.
2002,
67:
5553
<A NAME="RE11404SS-87">87 </A>
Jensen JF.
Johannsen M.
Org. Lett.
2003,
5:
3025
<A NAME="RE11404SS-88">88 </A>
Cammidge AN.
Crépy KVL.
Chem. Commun.
2000,
1723
<A NAME="RE11404SS-89">89 </A>
Bei X.
Crevier T.
Guram AS.
Jandeleit B.
Powers TS.
Turner HW.
Uno T.
Weinberg WH.
Tetrahedron Lett.
1999,
40:
3855
<A NAME="RE11404SS-90">90 </A>
Bei X.
Turner HW.
Weinberg WH.
Guram AS.
Petersen JL.
J. Org. Chem.
1999,
64:
6797
<A NAME="RE11404SS-91">91 </A>
Clarke ML.
Cole-Hamilton DJ.
Woollins JD.
J. Chem. Soc., Dalton Trans.
2001,
2721
<A NAME="RE11404SS-92">92 </A>
Cheng J.
Wang F.
Xu J.-H.
Pan Y.
Zhang Z.
Tetrahedron Lett.
2003,
44:
7095
<A NAME="RE11404SS-93">93 </A>
Urgaonkar S.
Nagarajan M.
Verkade JG.
Tetrahedron Lett.
2002,
43:
8921
94a </A>
Widdowson DA.
Wilhelm R.
Chem. Commun.
2003,
578
94b </A>
Wilhelm R.
Widdowson DA.
J. Chem. Soc., Perkin Trans. 1
2000,
3808
94c </A>
Widdowson DA.
Wilhelm R.
Chem. Commun.
1999,
2211
95a </A>
Hegedus LS. In
Organometallics in Synthesis: A Manual
2nd ed.:
Schlosser M.
Wiley;
New York:
2002.
p.1123-1217
95b </A>
Grushin VV.
Chem.-Eur. J.
2002,
8:
1006
<A NAME="RE11404SS-96">96 </A>
Kim YM.
Yu S.
J. Am. Chem. Soc.
2003,
125:
1696
<A NAME="RE11404SS-97">97 </A>
Retboll M.
Edwards AJ.
Rae AD.
Willis AC.
Bennett MA.
Wenger E.
J. Am. Chem. Soc.
2002,
124:
8348
<A NAME="RE11404SS-98">98 </A>
Regitz M.
Angew. Chem., Int. Ed. Engl.
1996,
35:
725
<A NAME="RE11404SS-99">99 </A>
Herrmann WA.
Angew. Chem. Int. Ed.
2002,
41:
1290
<A NAME="RE11404SS-100">100 </A>
Hillier AC.
Grasa GA.
Viciu MS.
Lee HM.
Yang C.
Nolan SP.
J. Organomet. Chem.
2002,
653:
69
<A NAME="RE11404SS-101">101 </A>
Weskamp T.
Kohl FJ.
Hieringer W.
Gleich D.
Herrmann WA.
Angew. Chem. Int. Ed.
1999,
38:
241
<A NAME="RE11404SS-102">102 </A>
Grasa GA.
Viciu MS.
Huang J.
Zhang C.
Trudell ML.
Nolan SP.
Organometallics
2002,
21:
2866
<A NAME="RE11404SS-103">103 </A>
Herrmann WA.
Reisinger C.-P.
Spiegler M.
J. Organomet. Chem.
1998,
557:
93
<A NAME="RE11404SS-104">104 </A>
Zhang C.
Huang J.
Trudell ML.
Nolan SP.
J. Org. Chem.
1999,
64:
3804
<A NAME="RE11404SS-105">105 </A>
Ding S.
Gray NS.
Ding Q.
Schultz PG.
Tetrahedron Lett.
2001,
42:
8751
<A NAME="RE11404SS-106">106 </A>
Zhang C.
Trudell ML.
Tetrahedron Lett.
2000,
41:
595
<A NAME="RE11404SS-107">107 </A>
Fürstner A.
Leitner A.
Synlett
2001,
290
<A NAME="RE11404SS-108">108 </A>
Böhm VPW.
Gstöttmayr CWK.
Weskamp T.
Herrmann WA.
J. Organomet. Chem.
2000,
595:
186
<A NAME="RE11404SS-109">109 </A>
Gstöttmayr CWK.
Böhm VPW.
Herdtweck E.
Grosche M.
Herrmann WA.
Angew. Chem. Int. Ed.
2002,
41:
1364
<A NAME="RE11404SS-110">110 </A>
Weskamp T.
Böhm VPW.
Herrmann WA.
J. Organomet. Chem.
1999,
585:
348
<A NAME="RE11404SS-111">111 </A>
Herrmann WA.
Böhm VPW.
Gstöttmayr CWK.
Grosche M.
Reisinger C.-P.
Weskamp T.
J. Organomet. Chem.
2001,
617-618:
616
<A NAME="RE11404SS-112">112 </A>
Altenhoff G.
Goddard R.
Lehmann CW.
Glorius F.
Angew. Chem. Int. Ed.
2003,
42:
3690
<A NAME="RE11404SS-113">113 </A>
Schwarz J.
Böhm VPW.
Gardiner MG.
Grosche M.
Herrmann WA.
Hieringer W.
Raudaschl-Sieber G.
Chem.-Eur. J.
2000,
6:
1773
<A NAME="RE11404SS-114">114 </A>
Lin K.
Song M.
Cai M.
Hao X.
Wu Y.
Tetrahedron Lett.
2003,
44:
3955
<A NAME="RE11404SS-115">115 </A>
Byun J.-W.
Lee Y.-S.
Tetrahedron Lett.
2004,
45:
1837
<A NAME="RE11404SS-116">116 </A>
Mathews CJ.
Smith PJ.
Welton T.
Chem. Commun.
2000,
1249
<A NAME="RE11404SS-117">117 </A>
Mathews CJ.
Smith PJ.
Welton T.
White AJP.
Williams DJ.
Organometallics
2001,
20:
3848
<A NAME="RE11404SS-118">118 </A>
McLachlan F.
Mathews CJ.
Smith PJ.
Welton T.
Organometallics
2003,
22:
5350
<A NAME="RE11404SS-119">119 </A>
Casalnuovo AL.
Calabrese JC.
J. Am. Chem. Soc.
1990,
112:
4324
<A NAME="RE11404SS-120">120 </A>
Wallow TI.
Novak BM.
J. Am. Chem. Soc.
1991,
113:
7411
<A NAME="RE11404SS-121">121 </A>
Genêt JP.
Linquist A.
Blart E.
Mouriès V.
Savignac M.
Vaultier M.
Tetrahedron Lett.
1995,
36:
1443
<A NAME="RE11404SS-122">122 </A>
Genêt JP.
Blart E.
Savignac M.
Synlett
1992,
715
<A NAME="RE11404SS-123">123 </A>
Dupuis C.
Adiey K.
Charruault L.
Michelet V.
Savignac M.
Genêt JP.
Tetrahedron Lett.
2001,
42:
6523
<A NAME="RE11404SS-124">124 </A>
Paetzold E.
Oehme G.
J. Mol. Catal. A: Chem.
2000,
152:
69
<A NAME="RE11404SS-125">125 </A>
Beller M.
Krauter JGE.
Zapf A.
Angew. Chem., Int. Ed. Engl.
1997,
36:
772
<A NAME="RE11404SS-126">126 </A>
Ueda M.
Nishimura M.
Miyaura N.
Synlett
2000,
856
<A NAME="RE11404SS-127">127 </A>
Uozumi Y.
Danjo H.
Hayashi T.
J. Org. Chem.
1999,
64:
3384
<A NAME="RE11404SS-128">128 </A>
Shaughnessy KH.
Booth RS.
Org. Lett.
2001,
3:
2757
<A NAME="RE11404SS-129">129 </A>
Moore LR.
Shaughnessy KH.
Org. Lett.
2004,
6:
225
<A NAME="RE11404SS-130">130 </A>
Wallow TI.
Novak BM.
J. Org. Chem.
1994,
59:
5034
<A NAME="RE11404SS-131">131 </A>
Kong K.-C.
Cheng C.-H.
J. Am. Chem. Soc.
1991,
113:
6313
<A NAME="RE11404SS-132">132 </A>
Herrmann WA.
Brossmer C.
Priermeier T.
Öfele K.
J. Organomet. Chem.
1994,
481:
97
<A NAME="RE11404SS-133">133 </A>
Migita T.
Nagai T.
Kiuchi K.
Kosugi M.
Bull. Chem. Soc. Jpn.
1983,
56:
2869
<A NAME="RE11404SS-134">134 </A>
Beletskaya IP.
J. Organomet. Chem.
1983,
250:
551
<A NAME="RE11404SS-135">135 </A>
Marck G.
Villiger A.
Buchecker R.
Tetrahedron Lett.
1994,
35:
3277
<A NAME="RE11404SS-136">136 </A>
Moreno-Mañas M.
Pajuelo F.
Pleixats R.
J. Org. Chem.
1995,
60:
2396
<A NAME="RE11404SS-137">137 </A>
O’Keefe DF.
Dannock MC.
Marcuccio SM.
Tetrahedron Lett.
1992,
33:
6679
<A NAME="RE11404SS-138">138 </A>
Goodson FE.
Wallow TI.
Novak BM.
Org. Synth.
1998,
75:
61
<A NAME="RE11404SS-139">139 </A>
Badone D.
Baroni M.
Cardamone R.
Ielmini A.
Guzzi U.
J. Org. Chem.
1997,
62:
7170
<A NAME="RE11404SS-140">140 </A>
Bussolari JC.
Rehborn DC.
Org. Lett.
1999,
1:
965
<A NAME="RE11404SS-141">141 </A>
Bumagin NA.
Bykov VV.
Tetrahedron
1997,
53:
14437
<A NAME="RE11404SS-142">142 </A>
Campi EM.
Jackson WR.
Marcuccio SM.
Naeslund CGM.
J. Chem. Soc., Chem. Commun.
1994,
2395
<A NAME="RE11404SS-143">143 </A>
Taylor PN.
O’Connell MJ.
McNeill LA.
Hall MJ.
Aplin RT.
Anderson HL.
Angew. Chem. Int. Ed.
2000,
39:
3456
<A NAME="RE11404SS-144">144 </A>
Turrin C.-O.
Chiffre J.
Daran J.-C.
de Montauzon D.
Caminade A.-M.
Manoury E.
Balavoine G.
Majoral J.-P.
Tetrahedron
2001,
57:
2521
<A NAME="RE11404SS-145">145 </A>
Mamane V.
Riant O.
Tetrahedron
2001,
57:
2555
<A NAME="RE11404SS-146">146 </A>
Molander GA.
Biolatto B.
Org. Lett.
2002,
4:
1867
<A NAME="RE11404SS-147">147 </A>
Darses S.
Jeffery T.
Genêt J.-P.
Brayer J.-L.
Demoute J.-P.
Tetrahedron Lett.
1996,
37:
3857
<A NAME="RE11404SS-148">148 </A>
Sengupta S.
Bhattacharyya S.
J. Org. Chem.
1997,
62:
3405
<A NAME="RE11404SS-149">149 </A>
Christoforou IC.
Koutentis PA.
Rees CW.
Org. Biomol. Chem.
2003,
1:
2900
<A NAME="RE11404SS-150">150 </A>
Bedford RB.
Blake ME.
Butts CP.
Holder D.
Chem. Commun.
2003,
466
<A NAME="RE11404SS-151">151 </A>
Hesse S.
Kirsch G.
Synthesis
2001,
755
<A NAME="RE11404SS-152">152 </A>
Moreno-Mañas M.
Pérez M.
Pleixats R.
J. Org. Chem.
1996,
61:
2346
<A NAME="RE11404SS-153">153 </A>
Smith KA.
Campi EM.
Jackson WR.
Marcuccio S.
Naeslund CGM.
Deacon GB.
Synlett
1997,
131
<A NAME="RE11404SS-154">154 </A>
Deng Y.
Gong L.
Mi A.
Liu H.
Jang Y.
Synthesis
2003,
337
<A NAME="RE11404SS-155">155 </A>
Tao X.
Zhao Y.
Shen D.
Synlett
2004,
359
<A NAME="RE11404SS-156">156 </A>
Bumagin NA.
Korolev DN.
Tetrahedron Lett.
1999,
40:
3057
<A NAME="RE11404SS-157">157 </A>
Walsh CJ.
Mandal BK.
Chem. Mater.
2001,
13:
2472
<A NAME="RE11404SS-158">158 </A>
McClure MS.
Roschangar F.
Hodson SJ.
Millar A.
Osterhout MH.
Synthesis
2001,
1681
<A NAME="RE11404SS-159">159 </A>
Leadbeater NE.
Marco M.
Org. Lett.
2002,
4:
2973
<A NAME="RE11404SS-160">160 </A>
Leadbeater NE.
Marco M.
Angew. Chem. Int. Ed.
2003,
42:
1407
<A NAME="RE11404SS-161">161 </A>
Blettner CG.
König WA.
Stenzel W.
Schotten T.
J. Org. Chem.
1999,
64:
3885
<A NAME="RE11404SS-162">162 </A>
Blettner CG.
König WA.
Rühter G.
Stenzel W.
Schotten T.
Synlett
1999,
307
<A NAME="RE11404SS-163">163 </A>
Villemin D.
Gómez-Escalonilla MJ.
Saint-Clair J.-F.
Tetrahedron Lett.
2001,
42:
635
<A NAME="RE11404SS-164">164 </A>
Zim D.
Monteiro AL.
Dupont J.
Tetrahedron Lett.
2000,
41:
8199
<A NAME="RE11404SS-165">165 </A>
Kabalka GW.
Namboodiri V.
Wang L.
Chem. Commun.
2001,
775
<A NAME="RE11404SS-166">166 </A>
Kabalka GW.
Pagni RM.
Hair CM.
Org. Lett.
1999,
1:
1423
<A NAME="RE11404SS-167">167 </A>
Kabalka GW.
Wang L.
Pagni RM.
Hair CM.
Namboodiri V.
Synthesis
2003,
217
<A NAME="RE11404SS-168">168 </A>
Villemin D.
Caillot F.
Tetrahedron Lett.
2001,
42:
639
<A NAME="RE11404SS-169">169 </A>
Gala D.
Stamford A.
Jenkins J.
Kugelman M.
Org. Process Res. Dev.
1997,
1:
163
<A NAME="RE11404SS-170">170 </A>
LeBlond CR.
Andrews AT.
Sun Y.
Sowa JR.
Org. Lett.
2001,
3:
1555
<A NAME="RE11404SS-171">171 </A>
Heidenreich RG.
Köhler K.
Krauter JGE.
Pietsch J.
Synlett
2002,
1118
<A NAME="RE11404SS-172">172 </A>
Li Y.
Hong XM.
Collard DM.
El-Sayed MA.
Org. Lett.
2000,
2:
2385
<A NAME="RE11404SS-173">173 </A>
Kim S.-W.
Kim M.
Lee WY.
Hyeon T.
J. Am. Chem. Soc.
2002,
124:
7642
<A NAME="RE11404SS-174">174 </A>
Liu Y.
Khemtong C.
Hu J.
Chem. Commun.
2004,
398
<A NAME="RE11404SS-175">175 </A>
Reetz MT.
Westermann E.
Angew. Chem. Int. Ed.
2000,
39:
165
<A NAME="RE11404SS-176">176 </A>
McNulty J.
Capretta A.
Wilson J.
Dyck J.
Adjabeng G.
Robertson A.
Chem. Commun.
2002,
1986
<A NAME="RE11404SS-177">177 </A>
Rajagopal R.
Jarikote DV.
Srinivasan KV.
Chem. Commun.
2002,
616
<A NAME="RE11404SS-178">178 </A>
Varma RS.
Naicker KP.
Tetrahedron Lett.
1999,
40:
439
<A NAME="RE11404SS-179">179 </A>
Paul S.
Clark JH.
Green Chem.
2003,
5:
635
<A NAME="RE11404SS-180">180 </A>
Yao M.-L.
Deng M.-Z.
J. Org. Chem.
2000,
65:
5034
<A NAME="RE11404SS-181">181 </A>
Bellina F.
Anselmi C.
Rossi R.
Tetrahedron Lett.
2001,
42:
3851
<A NAME="RE11404SS-182">182 </A>
Bellina F.
Anselmi C.
Viel S.
Mannina L.
Rossi R.
Tetrahedron
2001,
57:
9997
<A NAME="RE11404SS-183">183 </A>
Griffiths C.
Leadbeater NE.
Tetrahedron Lett.
2000,
41:
2487
<A NAME="RE11404SS-184">184 </A>
Zapf A.
Beller M.
Chem.-Eur. J.
2000,
6:
1830
<A NAME="RE11404SS-185">185 </A>
Andreu MG.
Zapf A.
Beller M.
Chem. Commun.
2000,
2475
<A NAME="RE11404SS-186">186 </A>
Li GY.
Angew. Chem. Int. Ed.
2001,
40:
1513
<A NAME="RE11404SS-187">187 </A>
Li GY.
J. Org. Chem.
2002,
67:
3643
<A NAME="RE11404SS-188">188 </A>
Grasa GA.
Hillier AC.
Nolan SP.
Org. Lett.
2001,
3:
1077
<A NAME="RE11404SS-189">189 </A>
Tao B.
Boykin DW.
Tetrahedron Lett.
2002,
43:
4955
<A NAME="RE11404SS-190">190 </A>
Feuerstein M.
Laurenti D.
Doucet H.
Santelli M.
Chem. Commun.
2001,
43
<A NAME="RE11404SS-191">191 </A>
Feuerstein M.
Laurenti D.
Bougeant C.
Doucet H.
Santelli M.
Chem. Commun.
2001,
325
<A NAME="RE11404SS-192">192 </A>
Feuerstein M.
Doucet H.
Santelli M.
Tetrahedron Lett.
2001,
42:
6667
<A NAME="RE11404SS-193">193 </A>
Feuerstein M.
Laurenti D.
Doucet H.
Santelli M.
Synthesis
2001,
2320
<A NAME="RE11404SS-194">194 </A>
Feuerstein M.
Doucet H.
Santelli M.
Tetrahedron Lett.
2001,
42:
5659
<A NAME="RE11404SS-195">195 </A>
Feuerstein M.
Doucet H.
Santelli M.
Synlett
2001,
1458
<A NAME="RE11404SS-196">196 </A>
Adjabeng G.
Brenstrum T.
Wilson J.
Framton C.
Robertson A.
Hillhouse J.
McNulty J.
Capretta A.
Org. Lett.
2003,
5:
953
<A NAME="RE11404SS-197">197 </A>
Nájera C.
G il-Moltó J.
Karlström S.
Falvella LR.
Org. Lett.
2003,
5:
1451
<A NAME="RE11404SS-198">198 </A>
Hong F.-E.
Ho Y.-J.
Chang Y.-C.
Lai Y.-C.
Tetrahedron
2004,
60:
2639
<A NAME="RE11404SS-199">199 </A>
Mobufu EB.
Clark JH.
Macquarrie DJ.
Green Chem.
2001,
3:
23
<A NAME="RE11404SS-200">200 </A>
Lan P.
Berta D.
Porco JA.
South MS.
Parlow JJ.
J. Org. Chem.
2003,
68:
9678
<A NAME="RE11404SS-201">201 </A>
Colacot TJ.
Gore ES.
Kuber A.
Organometallics
2002,
21:
3301
<A NAME="RE11404SS-202">202 </A>
Yamada YMA.
Takeda K.
Takahashi H.
Ikegami S.
J. Org. Chem.
2003,
68:
7733
<A NAME="RE11404SS-203">203 </A>
Hu Q.-S.
Lu Y.
Tang Z.-Y.
Yu H.-B.
J. Am. Chem. Soc.
2003,
125:
2856
<A NAME="RE11404SS-204">204 </A>
Willis MC.
Powell LHW.
Claverie CK.
Watson SJ.
Angew. Chem. Int. Ed.
2004,
43:
1249
<A NAME="RE11404SS-205">205 </A>
Hardy JJE.
Hubert S.
Macquarrie DJ.
Wilson AJ.
Green Chem.
2004,
6:
53
206a </A>
See ref. 127.
206b </A>
Kamatani A.
Overman LE.
J. Org. Chem.
1999,
64:
8743
206c </A>
Anderson JC.
Namli H.
Roberts CA.
Tetrahedron
1997,
44:
15123
