Abstract
Palladium-catalyzed alkynylation of aryl and hetaryl halides
has found wide application in the areas of synthetic, heterocyclic,
and medicinal chemistry. Attempts to introduce the stable and potentially
recyclable palladium/carbon has provided an attractive
alternative to the homogeneous palladium catalytic process. The
present article provides a personal account of the outcome of the
use of conventional palladium catalysts versus palladium/carbon,
especially under Sonogashira conditions.
1 Introduction
1.1 The Focus on Palladium/Carbon
1.2 The Origin of the Research
2 Copper-Free Sonogashira Coupling: An Unusual Observation
3 Palladium-Mediated Synthesis of 3-Substituted (Thio)flavones:
The Role of (S)-Prolinol and Copper
4 Palladium/Carbon in Water
4.1 Synthesis of Benzo[b]furans
4.2 2-Aminoethanol as an Alternative Base: Synthesis of Aryl- and
Hetaryl-Substituted Alkynes
4.3 Synthesis of Indoles
5 Palladium/Carbon in Organic Solvents
5.1 Synthesis of Isocoumarins and Phthalides
5.2 Synthesis of Thieno[2,3-c]pyranones
5.3 Synthesis of Alkynylpyrimidines
5.4 Synthesis of Furoquinolines and Pyrroloquinolines
5.5 Synthesis of 2H-1,2-Benzothiazine
1,1-Dioxides
6 Alkynylation of b-Chloroacroleins
7 Synthesis of Substituted Benzenes Fused with Carbocycles/Heterocycles:
Palladium Salts versus Palladium/Carbon
8 Palladium/Carbon in the Union of Organic Azide and
Terminal Alkynes
9 Conclusions: Towards Fulfilling the Requirements for Commercialization
Key words
catalysis - palladium - palladium/carbon - alkynylation - aryl halides - Sonogashira
reaction
References
<A NAME="RA53509ST-1">1</A>
Present address: Institute of Life
Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad
500046, Andhra Pradesh, India; Fax +914066571581.
<A NAME="RA53509ST-2A">2a</A>
Sonogashira K.
Tohda Y.
Hagihara N.
Tetrahedron Lett.
1975,
4467
<A NAME="RA53509ST-2B">2b</A>
Sonogashira K.
Yatake T.
Tohda Y.
Takahashi S.
Hagihara N.
J. Chem.
Soc., Chem. Commun.
1977,
291
<A NAME="RA53509ST-2C">2c</A>
Takahashi S.
Kuroyama Y.
Sonogashira K.
Hagihara N.
Synthesis
1980,
627
<A NAME="RA53509ST-3">3</A>
Dasgupta SK.
Pal M.
Mahanty JS.
Kundu NG.
Novel 5-Substituted
Uracil Derivatives as Inhibitors of Thymidylate Synthesis Enzyme
Paper
number CP22:
15th National Symposium on Organic Chemistry
(NASOC-XV);
Calcutta: March 22-23, 1994.
<A NAME="RA53509ST-4">4</A>
Kundu NG.
Das B.
Spears CP.
Majumdar A.
Kang SI.
J.
Med. Chem.
1990,
33:
1975
<A NAME="RA53509ST-5A">5a</A>
Kundu NG.
Dasgupta SK.
J. Chem. Soc., Perkin Trans. 1
1993,
2657
<A NAME="RA53509ST-5B">5b</A>
Kundu NG.
Pal M.
Chowdhury C.
J. Chem. Res., Synop.
1995,
4
<A NAME="RA53509ST-6">6</A>
Stephens RD.
Castro CE.
J. Org. Chem.
1963,
28:
3313
<A NAME="RA53509ST-7">7</A>
Robins MJ.
Barr PJ.
J. Org. Chem.
1983,
48:
1854
<A NAME="RA53509ST-8">8</A>
Kundu NG.
Pal M.
Mahanty JS.
Dasgupta SK.
J. Chem. Soc.,
Chem. Commun.
1992,
41
<A NAME="RA53509ST-9">9</A>
Kundu NG.
Pal M.
Mahanty JS.
De M.
J. Chem. Soc., Perkin Trans. 1
1997,
2815
<A NAME="RA53509ST-10">10</A>
Kundu NG.
Pal M.
J. Chem. Soc., Chem. Commun.
1993,
86
<A NAME="RA53509ST-11">11</A>
Kundu NG.
Pal M.
Nandi B.
J.
Chem. Soc., Perkin Trans. 1
1998,
561
<A NAME="RA53509ST-12">12</A>
Arcadi A.
Cacchi S.
Marinelli F.
Synthesis
1986,
749
<A NAME="RA53509ST-13">13</A>
Kundu NG.
Pal M.
Chowdhury C.
J.
Chem. Res.
1993,
432
<A NAME="RA53509ST-14">14</A>
Rossi R.
Carpita A.
Bigelli C.
Tetrahedron
Lett.
1985,
26:
523
<A NAME="RA53509ST-15">15</A>
Pal M.
Kundu NG.
J. Chem. Soc., Perkin Trans. 1
1996,
449
<A NAME="RA53509ST-16A">16a</A>
Alonso F.
Beletskaya IP.
Yus M.
Chem. Rev.
2004,
104:
3079
<A NAME="RA53509ST-16B">16b</A>
Krisch G.
Hesse S.
Comel A.
Curr.
Org. Synth.
2004,
1:
47
<A NAME="RA53509ST-17">17</A>
Zeni G.
Larock RC.
Chem. Rev.
2006,
106:
4644
<A NAME="RA53509ST-18">18</A>
Patil NT.
Yamamoto Y.
Chem. Rev.
2008,
108:
3395
<A NAME="RA53509ST-19">19</A>
Chinchilla R.
Nájera C.
Chem. Rev.
2007,
107:
874
<A NAME="RA53509ST-20A">20a</A>
De la Rosa MA.
Velarde E.
Guzman A.
Synth. Commun.
1990,
20:
2059
<A NAME="RA53509ST-20B">20b</A>
Novak Z.
Szabo A.
Repasi J.
Kotschy A.
J. Org. Chem.
2003,
68:
3327
For the use of Pd(OH)2/C as catalyst,
see:
<A NAME="RA53509ST-20C">20c</A>
Mori Y.
Seki M.
J. Org. Chem.
2003,
68:
1571
<A NAME="RA53509ST-20D">20d</A>
Heidenreich RG.
Köhler K.
Krauter JGE.
Pietsch J.
Synlett
2002,
1118
<A NAME="RA53509ST-20E">20e</A>
Felpin F.-X.
Vo-Thanh G.
Villiéras J.
Lebreton J.
Tetrahedron: Asymmetry
2001,
12:
1121
<A NAME="RA53509ST-20F">20f</A>
Bates RW.
Boonsombat J.
J. Chem.
Soc., Perkin Trans. 1
2001,
654
<A NAME="RA53509ST-20G">20g</A>
Bleicher LS.
Cosford NDP.
Herbaut A.
McCallum JS.
McDonald IA.
J. Org. Chem.
1998,
63:
1109
<A NAME="RA53509ST-20H">20h</A>
Bleicher L.
Cosford NDP.
Synlett
1995,
1115
<A NAME="RA53509ST-20I">20i</A>
Potts KT.
Horwitz CP.
Fessak A.
Keshavarz KM.
Nash KE.
Toscano PJ.
J.
Am. Chem. Soc.
1993,
115:
10444
<A NAME="RA53509ST-21">21</A>
Yin LX.
Liebscher J.
Chem. Rev.
2007,
107:
133
<A NAME="RA53509ST-22">22</A>
Seki M.
Synthesis
2006,
2975
<A NAME="RA53509ST-23A">23a</A>
Pal M.
Parasuraman K.
Gupta S.
Yeleswarapu KR.
Synlett
2002,
1976
For a review, see:
<A NAME="RA53509ST-23B">23b</A>
Pal M.
Tetrahedron
2009,
65:
433
<A NAME="RA53509ST-24">24</A>
Rao YK,
Pal M,
Sharma VM,
Venkateswarlu A, and
Pillaresetti R. inventors; Patent
Application US 2005/0119269 A1.
June
2
<A NAME="RA53509ST-25">25</A>
Pal M.
Subramanian V.
Parasuraman K.
Yeleswarapu KR.
Tetrahedron
2003,
59:
9563
<A NAME="RA53509ST-26">26</A>
Kalai T.
Kulcsar G.
Osz E.
Jeko J.
Sumegi B.
Hideg K.
Arkivoc
2004,
(vii):
266
<A NAME="RA53509ST-27">27</A>
Pal M.
Dakarapu R.
Parasuraman K.
Subramanian V.
Yeleswarapu KR.
J.
Org. Chem.
2005,
70:
7179
<A NAME="RA53509ST-28">28</A>
Pal M.
Parasuraman K.
Subramanian V.
Dakarapu R.
Yeleswarapu KR.
Tetrahedron
Lett.
2004,
45:
2305
<A NAME="RA53509ST-29">29</A>
Li C.-J.
Chem.
Rev.
2005,
105:
3095
<A NAME="RA53509ST-30">30</A>
Bhattacharya S.
Sengupta S.
Tetrahedron Lett.
2004,
45:
8733
<A NAME="RA53509ST-31">31</A>
Cacchi S.
Fabrizi G.
Goggiamani A.
Curr.
Org. Chem.
2006,
10:
1423
<A NAME="RA53509ST-32">32</A>
Dai W.-M.
Lai KW.
Tetrahedron Lett.
2002,
43:
9377
<A NAME="RA53509ST-33A">33a</A>
Pal M.
Subramanian V.
Yeleswarapu KR.
Tetrahedron Lett.
2003,
44:
8221
<A NAME="RA53509ST-33B">33b</A>
Xu G.
Searle LL.
Hughes TV.
Beck AK.
Connolly PJ.
Abad MC.
Neeper MP.
Struble GT.
Springer BA.
Emanuel
SL.
Gruninger RH.
Pandey N.
Adams M.
Moreno-Mazza S.
Fuentes-Pesquera AR.
Middleton SA.
Greenberger LM.
Bioorg. Med. Chem. Lett.
2008,
18:
3495
<A NAME="RA53509ST-34A">34a</A>
Heidenreich R.-G.
Krauter JGE.
Pietsch J.
Köheler K.
J. Mol. Catal. A: Chem.
2002,
182-183:
499
<A NAME="RA53509ST-34B">34b</A>
Tagata T.
Nishida M.
J. Org. Chem.
2003,
68:
9412
<A NAME="RA53509ST-35A">35a</A>
Pal M.
Batchu VR.
Subramanian V.
Parasuraman K.
Swamy NK.
Kumar S.
Tetrahedron
2005,
61:
9869
<A NAME="RA53509ST-35B">35b</A>
Subramanian V.
Batchu VR.
Pal M.
An Improved Synthesis of 2-Substituted Benzo[b]furans in Water under Pd/C-Cu
Catalysis
Paper number P15:
Indo-US Conference
on Recent Advances in Organometallic Catalysis and Olefin Polymerization;
IIT
Madras / Chennai / India: December 10-12, 2003.
<A NAME="RA53509ST-35C">35c</A>
Bong DT.
Ghadiri
MR.
Org.
Lett.
2001,
3:
2509
<A NAME="RA53509ST-35D">35d</A>
Raju S.
Kumar PR.
Mukkanti K.
Annamalai P.
Pal M.
Bioorg.
Med. Chem. Lett.
2006,
6185
<A NAME="RA53509ST-36A">36a</A>
Reddy EA.
Barange DK.
Islam A.
Mukkanti K.
Pal M.
Tetrahedron
2008,
64:
7143
<A NAME="RA53509ST-36B">36b</A>
Reddy EA.
Islam A.
Mukkanti K.
Bandameedi V.
Bhownik DR.
Pal M.
Beilstein
J. Org. Chem.
2009,
5: No32 (DOI: 10.3762/bjoc.5.32)
<A NAME="RA53509ST-37A">37a</A>
Nolan JM.
Comins DL.
J. Org. Chem.
2003,
68:
3736
<A NAME="RA53509ST-37B">37b</A>
Elangoven A.
Chen T.-Y.
Chen C.-Y.
Ho
T.-I.
Chem. Commun.
2003,
2146
<A NAME="RA53509ST-37C">37c</A>
Seck M.
Franck X.
Hocquemiller R.
Figadère B.
Peyrat J.-F.
Provot O.
Brion J.-D.
Alami M.
Tetrahedron Lett.
2004,
45:
1881
<A NAME="RA53509ST-37D">37d</A>
Rodriguez JG.
de los Rios C.
Lafuente A.
Tetrahedron
2005,
61:
9042
<A NAME="RA53509ST-37E">37e</A>
Toyota M.
Komori C.
Ihara M.
J.
Org. Chem.
2000,
65:
7110
<A NAME="RA53509ST-37F">37f</A>
Ciufolini MA.
Mitchell JW.
Roschangar F.
Tetrahedron Lett.
1996,
37:
8281
<A NAME="RA53509ST-37G">37g</A>
Yamanaka H.
Shiraiwa M.
Edo K.
Sakamoto T.
Chem. Pharm. Bull.
1979,
27:
270
<A NAME="RA53509ST-37H">37h</A>
Belmont P.
Andrez J.-C.
Allan CSM.
Tetrahedron Lett.
2004,
45:
2783
<A NAME="RA53509ST-38">38</A>
Cacchi S.
Fabrizi G.
Chem. Rev.
2005,
105:
2873
<A NAME="RA53509ST-39">39</A>
Patil S.
Buolamwini JK.
Curr. Org. Synth.
2006,
3:
477
<A NAME="RA53509ST-40">40</A>
Pal M.
Subramanian V.
Batchu VR.
Dager I.
Synlett
2004,
1965
<A NAME="RA53509ST-41">41</A>
Sakamoto T.
Kondo Y.
Iwashita S.
Nagano T.
Yamanaka H.
Chem.
Pharm. Bull.
1988,
36:
1305
<A NAME="RA53509ST-42">42</A>
Amjad M.
Knight DW.
Tetrahedron Lett.
2004,
45:
539
<A NAME="RA53509ST-43">43</A>
Mackman RL.
Katz BA.
Breitenbucher JG.
Hui HC.
Verner E.
Luong C.
Liu L.
Sprengeler PA.
J. Med. Chem.
2001,
44:
3856
<A NAME="RA53509ST-44">44</A>
Kundu NG.
Mahanty JS.
Das P.
Das B.
Tetrahedron Lett.
1993,
34:
1625
<A NAME="RA53509ST-45">45</A>
Takeda A.
Kamijo S.
Yamamoto Y.
J.
Am. Chem. Soc.
2000,
122:
5662
<A NAME="RA53509ST-46">46</A>
Liao H.-Y.
Cheng C.-H.
J. Org. Chem.
1995,
60:
3711
<A NAME="RA53509ST-47">47</A>
Kanazawa C.
Terada M.
Tetrahedron Lett.
2007,
48:
933
<A NAME="RA53509ST-48">48</A>
Uchiyama M.
Ozawa H.
Takuma K.
Matsumoto Y.
Yonehara M.
Hiroya K.
Sakamoto T.
Org. Lett.
2006,
8:
5517
<A NAME="RA53509ST-49A">49a</A>
Barange DK.
Batchu VR.
Pal M.
First Pd/C-Mediated
Synthesis of (Z)-3-Alkynylidene Phthalides
Joint International
Conference on Building Bridges Forging Bonds (ACS-CSIR OCCB);
Pune / India: January
7-9, 2006.
<A NAME="RA53509ST-49B">49b</A>
Zhou L.
Jiang H.-F.
Tetrahedron Lett.
2007,
48:
8449
<A NAME="RA53509ST-50">50</A>
Raju S.
Batchu VR.
Swamy NK.
Dev RV.
Babu JM.
Kumar PR.
Mukkanti K.
Pal M.
Tetrahedron
Lett.
2006,
47:
83
<A NAME="RA53509ST-51A">51a</A>
Raju S.
Batchu VR.
Swamy NK.
Dev RV.
Sreekanth BR.
Babu JM.
Vyas K.
Kumar PR.
Mukkanti K.
Annamalai P.
Pal M.
Tetrahedron
2006,
62:
9554
<A NAME="RA53509ST-51B">51b</A>
Queiroz M.-JRP.
Calhelha RC.
Vale-Silva LA.
Pinto E.
Nascimento MS.-J.
Eur. J. Med.
Chem.
2009,
44:
1893
<A NAME="RA53509ST-52A">52a</A>
Pal M,
Kalleda S,
Padakanti S,
Kumara Swamy N,
Yeleswarapu KR,
Alexander CW,
Khanna I,
Iqbal J,
Pillarisetti S, and
Barange D. inventors; Patent
Application US 2006/0084645 A1.
April
20,
<A NAME="RA53509ST-52B">52b</A>
Pal M.
Batchu VR.
Swamy NK.
Padakanti S.
Tetrahedron
Lett.
2006,
47:
3923
<A NAME="RA53509ST-53A">53a</A>
McGuigan C.
Barucki H.
Blewett S.
Carangio A.
Erichsen JT.
Andrei G.
Snoeck R.
De Clercq E.
Balzarini J.
J. Med. Chem.
2000,
43:
4993
<A NAME="RA53509ST-53B">53b</A>
McGuigan C.
Brancale A.
Andrei G.
Snoeck R.
De Clercq E.
Balzarini J.
Bioorg. Med. Chem. Lett.
2000,
10:
1215
<A NAME="RA53509ST-53C">53c</A>
McGuigan C.
Yarnold CJ.
Jones G.
Velazquez S.
Barucki H.
Brancale A.
Andrei G.
Snoeck R.
De Clercq E.
Balzarini J.
J. Med. Chem.
1999,
42:
4479
<A NAME="RA53509ST-53D">53d</A>
Janeba Z.
Balzarini J.
Andrei G.
Snoeck R.
De Clercq E.
Robins MJ.
J. Med. Chem.
2005,
48:
4690
<A NAME="RA53509ST-54A">54a</A>
Venkataraman S.
Barange DK.
Pal M.
Tetrahedron Lett.
2006,
47:
7317
<A NAME="RA53509ST-54B">54b</A>
Layek M.
Gajare V.
Kalita D.
Islam A.
Mukanti K.
Pal M.
Tetrahedron Lett.
2009,
50:
3867
See also
<A NAME="RA53509ST-54C">54c</A>
Layek M.
Rao A. VD.
Gajare V.
Kalita D.
Barenge DK.
Islam A.
Mukkanti K.
Pal M.
Tetrahedron Lett.
2009,
50:
4878
<A NAME="RA53509ST-55">55</A>
Harmata M.
Rayanil K.-o.
Gomes MG.
Zheng P.
Calkins NL.
Kim S.-Y.
Fan Y.
Bumbu V.
Lee DR.
Wacharasindhu S.
Hong X.
Org. Lett.
2005,
7:
143
For benzo[b]furans, see:
<A NAME="RA53509ST-56A">56a</A>
Banwell MG.
Flynn BL.
Willis AC.
Hamel E.
Aust.
J. Chem.
1999,
52:
767
<A NAME="RA53509ST-56B">56b</A>
Arcadi A.
Cacchi S.
Fabrizi G.
Marinelli F.
Moro L.
Synlett
1999,
1432
<A NAME="RA53509ST-56C">56c</A>
Colobert F.
Castanet A.-S.
Abillard O.
Eur.
J. Org. Chem.
2005,
3334
<A NAME="RA53509ST-56D">56d</A>
Yue D.
Yao T.
Larock RC.
J.
Org. Chem.
2005,
70:
10292
For benzo[b]thiophenes,
see:
<A NAME="RA53509ST-56E">56e</A>
Yue D.
Larock RC.
J. Org. Chem.
2002,
67:
1905
<A NAME="RA53509ST-56F">56f</A>
Hessian KO.
Flynn BL.
Org. Lett.
2003,
5:
4377
For furopyridines, see:
<A NAME="RA53509ST-57A">57a</A>
Arcadi A.
Cacchi S.
Di Giuseppe S.
Fabrizi G.
Marinelli F.
Org.
Lett.
2002,
4:
2409
For furoquinolines, see:
<A NAME="RA53509ST-57B">57b</A>
Aillaud I.
Bossharth E.
Conreaux D.
Desbordes P.
Monteiro N.
Balme G.
Org. Lett.
2006,
8:
1113
<A NAME="RA53509ST-58">58</A> For furopyrimidines, see:
Rao MS.
Esho N.
Sergeant C.
Roman D.
J. Org. Chem.
2003,
68:
6788
For indoles, see:
<A NAME="RA53509ST-59A">59a</A>
Yue D.
Larock RC.
Org. Lett.
2004,
6:
1037
<A NAME="RA53509ST-59B">59b</A>
Barluenga J.
Trincado M.
Rubio E.
Gonzalez JM.
Angew. Chem. Int.
Ed.
2003,
42:
2406
<A NAME="RA53509ST-59C">59c</A>
Yao D.
Yue D.
Larock RC.
J.
Comb. Chem.
2005,
7:
809
For isoquinolines and naphthyridines, see:
<A NAME="RA53509ST-59D">59d</A>
Huang Q.
Hunter JA.
Larock RC.
J. Org. Chem.
2002,
67:
3437
<A NAME="RA53509ST-60">60</A> For isoindolinones, see:
Yao T.
Larock RC.
J.
Org. Chem.
2005,
70:
1432
For isochromenes, see:
<A NAME="RA53509ST-61A">61a</A>
Barluenga J.
Vazquez-Villa H.
Ballesteros A.
Gonzalez JM.
J. Am. Chem. Soc.
2003,
125:
9028
<A NAME="RA53509ST-61B">61b</A>
Yue D.
Della Ca N.
Larock RC.
Org. Lett.
2004,
6:
1581
For isocoumarins, see:
<A NAME="RA53509ST-62A">62a</A>
Yao T.
Larock RC.
J. Org. Chem.
2003,
68:
5936
<A NAME="RA53509ST-62B">62b</A>
Rossi R.
Carpita A.
Bellina F.
Stabile P.
Mannina L.
Tetrahedron
2003,
59:
2067
For phosphaisocoumarins, see:
<A NAME="RA53509ST-62C">62c</A>
Peng A.-Y.
Ding Y.-X.
Org. Lett.
2004,
6:
1119
<A NAME="RA53509ST-63">63</A> For coumestans, see:
Yao T.
Yue D.
Larock RC.
J. Org. Chem.
2005,
70:
9985
For other examples of iodonium-promoted heterocyclizations
of acetylenic compounds, see:
<A NAME="RA53509ST-64A">64a</A>
Sniady A.
Wheeler KA.
Dembinski R.
Org.
Lett.
2005,
7:
1769
<A NAME="RA53509ST-64B">64b</A>
Liu Y.
Song F.
Cong L.
J.
Org. Chem.
2005,
70:
6999
<A NAME="RA53509ST-64C">64c</A>
Yao T.
Zhang X.
Larock RC.
J.
Org. Chem.
2005,
70:
7679
<A NAME="RA53509ST-64D">64d</A>
Liu Y.
Zhou S.
Org. Lett.
2005,
7:
4609
<A NAME="RA53509ST-64E">64e</A>
Waldo JP.
Larock RC.
Org.
Lett.
2005,
7:
5203
For iodocyclization of sulfonamide derivatives of
o-(alk-1-ynyl)anilines leading to 3-iodoindoles,
see:
<A NAME="RA53509ST-64F">64f</A>
Amjad M.
Knight DW.
Tetrahedron Lett.
2004,
45:
539
<A NAME="RA53509ST-65">65</A>
Barange DK.
Batchu VR.
Gorja D.
Pattabiraman VR.
Tatini LK.
Babu JM.
Pal M.
Tetrahedron
2007,
63:
1775
<A NAME="RA53509ST-66">66</A>
Barange DK.
Nishad TC.
Swamy NK.
Bandameedi V.
Kumar D.
Sreekanth BR.
Vyas K.
Pal M.
J. Org. Chem.
2007,
72:
8547
<A NAME="RA53509ST-67A">67a</A>
Hesse S.
Kirsch G.
Synthesis
2001,
755
<A NAME="RA53509ST-67B">67b</A>
Hesse S.
Kirsch G.
Tetrahedron Lett.
2002,
43:
1213
<A NAME="RA53509ST-67C">67c</A>
Hesse S.
Kirsch G.
Synthesis
2003,
717
<A NAME="RA53509ST-68">68</A>
Bera R.
Swamy NK.
Dhananjaya G.
Babu JM.
Kumar PR.
Mukkanti K.
Pal M.
Tetrahedron
2007,
63:
13018
<A NAME="RA53509ST-69A">69a</A>
Snieckus V.
Chem. Rev.
1990,
90:
879
<A NAME="RA53509ST-69B">69b</A>
Lautens M.
Klute W.
Tam W.
Chem.
Rev.
1996,
96:
49
<A NAME="RA53509ST-69C">69c</A>
Saito S.
Yamamoto Y.
Chem. Rev.
2000,
100:
2901
<A NAME="RA53509ST-69D">69d</A>
Yamamoto Y.
Ishii J.-I.
Nishiyama H.
Itoh K.
J. Am. Chem. Soc.
2004,
126:
3712
<A NAME="RA53509ST-70A">70a</A>
Saito S.
Chounan Y.
Nogami T.
Fukushi T.
Tsuboya N.
Yamada Y.
Kitahara H.
Yamamoto Y.
J. Org. Chem.
2000,
65:
5350
<A NAME="RA53509ST-70B">70b</A>
Gevorgyan V.
Tsuboya N.
Yamamoto Y.
J.
Org. Chem.
2001,
66:
2743
<A NAME="RA53509ST-70C">70c</A>
Saito S.
Salter MM.
Gevorgyan V.
Tsuboya N.
Tando K.
Yamamoto Y.
J. Am. Chem. Soc.
1996,
118:
3970 ; and references cited therein
<A NAME="RA53509ST-70D">70d</A>
Gevorgyan V.
Takeda A.
Homma M.
Sadayori N.
Radhakrishnan U.
Yamamoto Y.
J. Am. Chem. Soc.
1999,
121:
6391
For a sequential one-pot procedure
involving Sonogashira coupling and homo-benzannulation for the synthesis
of 6H-dibenzo[b,d]pyran-6-ones, see:
<A NAME="RA53509ST-71A">71a</A>
Kawasaki T.
Yamamoto Y.
J. Org. Chem.
2002,
67:
5138
<A NAME="RA53509ST-71B">71b</A>
Xi C.
Chen C.
Lin J.
Hong X.
Org. Lett.
2005,
7:
347
<A NAME="RA53509ST-72">72</A>
Swamy NK.
Tatini LK.
Babu JM.
Annamalai P.
Pal M.
Chem.
Commun.
2007,
1035
<A NAME="RA53509ST-73">73</A>
Batchu VR.
Barange DK.
Kumar D.
Sreekanth BR.
Vyas K.
Reddy EA.
Pal M.
Chem.
Commun.
2007,
1966
<A NAME="RA53509ST-74A">74a</A>
Rostovtsev VV.
Green LG.
Fokin VV.
Sharpless KB.
Angew. Chem. Int. Ed.
2002,
41:
2596
<A NAME="RA53509ST-74B">74b</A>
Tornøe
CW.
Christensen C.
Meldal M.
J. Org. Chem.
2002,
67:
3057
<A NAME="RA53509ST-74C">74c</A>
Kamijo S.
Jin T.
Huo Z.
Yamamoto Y.
J. Am. Chem. Soc.
2003,
125:
7786
<A NAME="RA53509ST-75">75</A>
Chowdhury C.
Mandal SB.
Achari B.
Tetrahedron
Lett.
2005,
46:
8531
