353
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Pd2dba3/P(t-Bu)3H.BF4/Cy2NMe Catalyzed Heck Coupling in Synthesis of 3-Alkenyl-1H-Isochromen-1-Ones

&
Pages 1048-1060 | Received 12 Dec 2019, Accepted 01 May 2020, Published online: 20 May 2020

References

  • (a) R. F. Heck, “Palladium-catalyzed reactions of organic halides with olefins”, Accounts of Chemical Research, 12, no. 4 (1979): 146–151, (b) I. P. Beletskaya and A. V. Cheprakov, “The Heck Reaction as a Sharpening Stone of Palladium Catalysis” Chemical Reviews, 100, no. 8 (2000): 3009-3066, (c) R. F. Heck, “Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives”, Journal of the American Chemical Society, 90, no. 20 (1968): 5518–5526, (d) R. F. Heck, “Allylation of aromatic compounds with organopalladium salts”, Journal of the American Chemical Society 90, no. 20 (1968): 5531–5534, (e) R. F. Heck, “The palladium-catalyzed arylation of enol esters, ethers, and halides. A new synthesis of 2-aryl aldehydes and ketones”, Journal of the American Chemical Society, 90, no. 20 (1968): 5535–5538, (f) R. F. Heck, “Aromatic haloethylation with palladium and copper halides”, Journal of the American Chemical Society, 90, no. 20 (1968): 5538–5542, (g) R. F. Heck, “The addition of alkyl- and arylpalladium chlorides to conjugated dienes”, Journal of the American Chemical Society, 90, no. 20 (1968): 5542–5546, (h) R. F. Heck, Mechanism of arylation and carbomethoxylation of olefins with organopalladium compounds”, Journal of the American Chemical Society, 91, no. 24 (1969): 6707–6714.
  • S. Brase and A. De Meijere, Metal-catalyzed cross-coupling reactions, edited by A. De Meijere, F. Diederich, vol. 1, 2nd ed. (Weinheim 2004), 217, WILEY‐VCH Verlag GmbH & Co, Germany.
  • K. C. Nicolaou, P. G. Bulger, and D. Sarlah, “Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis,”Angewandte Chemie (International ed. in English) 44, no. 29 (2005): 4442–89.
  • V. Farina, “High-Turnover Palladium Catalysts in Cross-Coupling and Heck Chemistry: A Critical Overview,”Advanced Synthesis & Catalysis 346, no. 13–15 (2004): 1553–82.
  • (a) B. J. Margolis, K. A. Long, D. L. T. Laird, J. C. Ruble and S. R. Pulley, “Assembly of 4-Aminoquinolines via Palladium Catalysis:  A Mild and Convenient Alternative to SNAr Methodology”, The Journal of Organic Chemistry, 72, no. 6 (2007): 2232–2235, (b) M. J. Burns, I. J. S. Fairlamb, A. R. Kapdi, P. Sehnal and R. J. K. Taylor, “Simple Palladium(II) Precatalyst for Suzuki−Miyaura Couplings:  Efficient Reactions of Benzylic, Aryl, Heteroaryl, and Vinyl Coupling”, Organic Letters, 9, no. 26 (2007): 5397–5400. (c) C. A. Flackenstein and H. Plenio, “Aqueous cross-coupling: highly efficient Suzuki–Miyaura coupling of N-heteroaryl halides and N-heteroarylboronic acids", Green Chemistry, 9, (2007): 1287–1291. (d) K. Pomeisl, A. Holy and R. Pohl, “Pd-catalyzed Suzuki–Miyaura coupling reactions in the synthesis of 5-aryl-1-[2-(phosphonomethoxy)ethyl]uracils as potential multisubstrate inhibitors of thymidine phosphorylase”, Tetrahedron Lett., 48, no. 17 (2007): 3065-3067. (e) M. Ruben and S. L. Buchwald, “Pd-Catalyzed Kumada−Corriu Cross-Coupling Reactions at Low Temperatures Allow the Use of Knochel-type Grignard Reagents”, Journal of the American Chemical Society, 129, no. 13 (2007): 3844–3845. (f) K. Billingsley and S. L. Buchwald, Journal of the American Chemical Society 129, no. 11 (2007):3358–3366. (g) D. Conreaux, E. Bossharth, N. Monteiro, P. Besbordes, J.-P. Vors and G. Balme, “Flexible Strategy for Differentially 3,5-Disubstituted 4-Oxypyridin-2(1H)-ones Based on Site-Selective Pd-Catalyzed Cross-Coupling Reactions”, Organic Letters, 9, no. 2 (2007): 271–274. (h) R. Pereira, A. Furst, B. Iglesias, P. Germain, H. Gronemeyer and A. R. de Lera, “Insights into the mechanism of the site-selective sequential palladium-catalyzed cross-coupling reactions of dibromothiophenes/dibromothiazoles and arylboronic acids. Synthesis of PPARβ/δ agonists”, Organic and Biomolecular Chemistry, 4, 2006, 4514–4525. (i) J. E. Utas, B. Olofson and B. Aakermark, “Efficient Synthesis of 2-Substituted Imidazoles by Palladium-Catalyzed Cross-Coupling with Benzylzinc Reagents”, Synlett, 12, (2006):1965–1967. (j) M. Romero, Y. Harrak,; J. Basset, L. Ginet, P. Constans and M. D. Pujol, "Preparation of N-arylpiperazines and other N-aryl compounds from aryl bromides as scaffolds of bioactive compounds”, Tetrahedron, 62, no. 38 (2006): 9010–9016. (k) M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O’Brien and C. Valente, “A User‐Friendly, All‐Purpose Pd–NHC (NHC=N‐Heterocyclic Carbene) Precatalyst for the Negishi Reaction: A Step Towards a Universal Cross‐Coupling Catalyst”, Chemistry A European Journal, 12, no. 18 (2006): 4749-4755. (l) P. Forgoine, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey and F. Bilodeau, “Unexpected Intermolecular Pd-Catalyzed Cross-Coupling Reaction Employing Heteroaromatic Carboxylic Acids as Coupling Partners”, Journal of the American Chemical Society, 128, no. 35 (2006):11350–11351. (m) K. Billingsley, K. W. Anderson and S. L. Buchwald, “A Highly Active Catalyst for Suzuki–Miyaura Cross‐Coupling Reactions of Heteroaryl Compounds", Angewandte Chemie International Edition, 45, no. 21 (2006): 3484–3488. (n) P. Prediger, A. V. Moro, C. W. Nogueira, L. Savegnago, P. H. Menezes, J. B. T. Rocha and G. Zeni, “Palladium-Catalyzed Suzuki Cross-Coupling of 2-Haloselenophenes:  Synthesis of 2-Arylselenophenes, 2,5-Diarylselenophenes, and 2-Arylselenophenyl Ketones”, The Journal of Organic Chemistry, 71, no. 10 (2006): 3786-3792. (o) S. E. Denmark and J. D. Baird, “Palladium-Catalyzed Cross-Coupling Reactions of Heterocyclic Silanolates with Substituted Aryl Iodides and Bromides”, Organic Letters,8, no. 4 (2006): 793–795.
  • X. Cui, J. Li, Z. P. Zhang, Y. Fu, L. Liu, and Q. X. Guo, “Pd(Quinoline-8-Carboxylate)(2) as a Low-Priced, Phosphine-Free Catalyst for Heck and Suzuki Reactions,”The Journal of Organic Chemistry 72, no. 24 (2007): 9342–5.
  • D. E. Bergbreiter, P. L. Osburn, and J. D. Frels, “Mechanistic Studies of SCS-Pd Complexes Used in Heck Catalysis,” Advanced Synthesis and Catalysis, 347, no. 1 (2005): 172–84.
  • M. L. Kantam, P. Srinivas, J. Yadav, P. R. Likhar, and S. Bhargava, “Trifunctional N,N,O-Terdentate Amido/Pyridyl Carboxylate Ligated Pd(II) Complexes for Heck and Suzuki Reactions,”The Journal of Organic Chemistry 74, no. 13 (2009): 4882–5.
  • B. Karimi, and D. Enders, “New N-Heterocyclic Carbene Palladium Complex/Ionic Liquid Matrix Immobilized on Silica: application as Recoverable Catalyst for the Heck Reaction,”Organic Letters 8, no. 6 (2006): 1237–40.
  • H. J. Li, and L. Wang, “Triethanolamine as an Efficient and Reusable Base, Ligand and Reaction Medium for Phosphane-Free Palladium-Catalyzed Heck Reactions,”European Journal of Organic Chemistry 2006, no. 22 (2006): 5099–102.
  • F. Y. Tsai, C. L. Wu, H. P. Lin, M. C. Chao, C. Y. Mou, and S. T. Liu, “Palladium Bipyridyl Complex Anchored on Nanosized MCM-41 as a Highly Efficient and Recyclable Catalyst for Heck Reaction,”Tetrahedron Letters, 45, no. 40 (2004): 7503–6.
  • C. P. Mehnert, D. W. Weaver, and J. Y. Ying, “Heterogeneous Heck Catalysis with Palladium-Grafted Molecular Sieves,”Journal of the American Chemical Society 120, no. 47 (1998): 12289–96.
  • D. E. Bergbreiter, P. L. Osburn, and J. D. Frels, “Nonpolar Polymers for Metal Sequestration and Ligand and Catalyst Recovery in Thermomorphic Systems,”Journal of the American Chemical Society 123, no. 44 (2001): 11105–6.
  • D. E. Bergbreiter, P. L. Osburn, and Y. S. Liu, “Tridentate SCS Palladium(II) Complexes: New, Highly Stable, Recyclable Catalysts for the Heck Reaction,”Journal of the American Chemical Society 121, no. 41 (1999): 9531–8.
  • M. Amini, M. Bagherzadeh, Z. M. Shoeili, and D. M. Boghaei, “Pd(OAc)2 without Added Ligand as an Active Catalyst for Mizoroki–Heck Reaction in Aqueous Media,”RSC Advances 2, no. 32 (2012): 12091–5.
  • L. M. Tao, Q. G. Li, W. Q. Liu, Y. Zhou, and J. F. Zhou, “Water-Promoted Palladium-Catalysed Heck Cross-Coupling Reactions of Aryl Halides with Alkenes in TBAB,” Journal of Chemical Research 35, no. 3 (2011): 154–6.
  • N. A. Bumagin, V. V. Bykov, L. I. Sukhomlinova, T. P. Tolstaya, and I. P. Beletskaya, “Palladium-Catalyzed Arylation of Styrene and Acrylic Acid in Water,” Journal of Organometallic Chemistry, 486, no. 1–2 (1995): 259–62.
  • (a) K. H. Shaughnessy, P. Kim and J. F. Hartwig, “A Fluorescence-Based Assay for High-Throughput Screening of Coupling Reactions. Application to Heck Chemistry”, Journal of the American Chemical Society, 121, no.10 (1999): 2123–2132. (b) A. Ehrentraut, A. Zapf and M. Beller, “A New Efficient Palladium Catalyst for Heck Reactions of Deactivated Aryl Chlorides”, Synlett, 11, (2000): 1589–1592. (c) G. Li, G. Zheng and A. F. Noonan, “Highly Active, Air-Stable Versatile Palladium Catalysts for the C−C, C−N, and C−S Bond Formations via Cross-Coupling Reactions of Aryl Chlorides”, The Journal of Organic Chemistry 66, no. 25 (2001): 8677–8681. (d) K. Selvakumar, A. Zapf and M. Beller, “New Palladium Carbene Catalysts for the Heck Reaction of Aryl Chlorides in Ionic Liquids”, Organic Letters, 4, no. 18 (2002): 3031–3033. (e) S. K. Yen, L. L. Koh, F. E. Hahn, H. V. Huynh and T. S. A. Hor, “Convenient Entry to Mono- and Dinuclear Palladium(II) Benzothiazolin-2-ylidene Complexes and Their Activities toward Heck Coupling", Organometallics,25, no. 21 (2006): 5105–5112. (f) J.-Y. Lee, P.-Y. Cheng, Y.-H. Tsai, G.-R. Lin, S.-P. Liu, M.-H. Sie and H. M. Lee, “Efficient Heck Reactions Catalyzed by Palladium(0) and -(II) Complexes Bearing N-Heterocyclic Carbene and Amide Functionalities”, Organometallics, 29, no. 17 (2010): 3901–3911.
  • (a) W. A. Herrmann, K. Ofele, S. K. Schneider, E. Herdtweck and S. D. Hoffmann, “A Carbocyclic Carbene as an Efficient Catalyst Ligand for C-C Coupling Reactions”, Angewandte Chemie International Edition, 45, no. 23 (2006): 3859–3862. (b) Q. Yao, M. Zabawa, J. Woo and C. Zheng, “Carbocyclic Carbene Ligands Derived from Aromatic Nitrones:  Formation and Catalytic Activity of Their Pd(II) Complexes”, Journal of the American Chemical Society, 129, no. 11 (2007): 3088-3089.
  • (a) A. F. Littke and G. C. Fu, “A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions”, Journal of the American Chemical Society, 123, no. 29 (2001): 6989–7000. (b) C. Yi and R. Hua, “An efficient palladium-catalyzed Heck coupling of aryl chlorides with alkenes”, Tetrahedron Letters, 47, no. 15 (2006): 2573-2576. (c) P. Srinivas, P. R. Likhar, H. Maheswaran, B. Sridhar, K. Ravikumar and M. L. Kantam, “N4‐Tetradentate Dicarboxyamidate/Dipyridyl Palladium Complexes as Robust Catalysts for the Heck Reaction of Deactivated Aryl Chlorides", Chemistry A European Journal,15, no. 2 (2009): 1578–1581. (d) C. R€ohlich and K. K€ohler, “Tetraalkylammonium‐Free Heck Olefination of Deactivated Chloroarenes by Using a Macrocyclic Catalyst Precursor", Chemistry A European Journal, 16, no. 8 (2010): 2363–2365.
  • M. R. Netherton and G. C. Fu, Organic Letters, 2001, 3, 4295–4298. 2002, 4, 95–97. (b) Nellisar D. Shashikumar, G Krishnamurthy, and Halehatti S. Bhojyanaik, Journal of Heterocyclic Chemistry, 2014, 51, 354–357
  • K. S. A. Vallin, P. Emilsson, M. Larhed, and A. Hallberg, “High-Speed Heck Reactions in Ionic Liquid with Controlled Microwave Heating,”The Journal of Organic Chemistry 67, no. 17 (2002): 6243–6.
  • M. Larhed, C. Moberg, and A. Hallberg, “Microwave-Accelerated Homogeneous Catalysis in Organic Chemistry,”Accounts of Chemical Research 35, no. 9 (2002): 717–27.
  • M. Larhed, “Uppsala University, Interfaculty Units, Acta Universitatis Upsaliensis” (Doctoral Thesis, 1997), 171.
  • Alois Fürstner, and Günter Seidel, “Microwave-Assisted Synthesis of Pinacol Boronates from Aryl Chlorides Catalyzed by a Palladium/Imidazolium Salt System,”Organic Letters 4, no. 4 (2002): 541–3.
  • B. M. Choudary, S. Madhi, N. S. Chowdari, M. L. Kantam, and B. Sreedhar, “Layered Double Hydroxide Supported Nanopalladium Catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-Type Coupling Reactions of Chloroarenes,”Journal of the American Chemical Society 124, no. 47 (2002): 14127–36.
  • J. B. Davison, N. M. Simon, and S. A. Sojka, “Palladium Catalyzed Olefin Arylation: extending the Scope of the Heck Reaction to Aryl Chlorides,” Journal of Molecular Catalysis, 22, no. 3 (1984): 349–52.
  • F. Alonso, I. P. Beletskaya, and M. Yus, “Non-Conventional Methodologies for Transition-Metal Catalysed Carbon–Carbon Coupling: A Critical Overview. Part 1: The Heck Reaction,”Tetrahedron 61, no. 50 (2005): 11771–835.
  • I. Ozdemir, N. Gurbuz, Y. Gok, and B. Cetinkaya, "N‐functionalized azolin‐2‐ylidene‐palladium‐catalyzed heck reaction", Heteroatom Chemistry, 19, no. 1 (2008): 82-86.
  • Eric Assen B. Kantchev, Christopher J. O'Brien, and Michael G. Organ, “Palladium Complexes of N-Heterocyclic Carbenes as Catalysts for Cross-Coupling Reactions-a Synthetic Chemist's Perspective,”Angewandte Chemie (International ed. in English) 46, no. 16 (2007): 2768–831.
  • T. Scherg, S. K. Schneider, G. D. Frey, J. Schwarz, E. Herdtweck, and W. A. Herrmann, “Bridged Imidazolium Salts Used as Precursors for Chelating Carbene Complexes of Palladium in the Mizoroki-Heck Reaction,”Synlett 2006, no. 18 (2006): 2894–907.
  • K. H. Shaughnessy, P. Kim, and J. F. Hartwig, “A Fluorescence-Based Assay for High-Throughput Screening of Coupling Reactions. Application to Heck Chemistry,”Journal of the American Chemical Society 121, no. 10 (1999): 2123–32.
  • James P. Stambuli, Christopher D. Incarvito, Michael Bühl, and John F. Hartwig, “Synthesis, Structure, Theoretical Studies, and Ligand Exchange Reactions of Monomeric, T-Shaped Arylpalladium(II) Halide Complexes with an Additional, Weak Agostic Interaction,”Journal of the American Chemical Society 126, no. 4 (2004): 1184–94.
  • Y. S. Kumar, C. Dasaradhan, K. Prabakaran, F. Nawaz Khan, E. D. Jeong, E. H. Chung, and, and H. G. Kim, “A Convenient and Efficient C–OH Bond Activation, PdCl 2 (PPh 3 ) 2 Catalyzed, C–C Bond Formation of Tautomerizable Quinolinones with the Aid of BOP Reagent and Boronic Acids,”RSC Advances, 4, no. 76 (2014): 40259–68.
  • K. Prabakaran, F. Nawaz Khan, and J. S. Jin, “An Efficient Copper-Free Pd(OAc)2/Ruphos-Catalyzed Sonogashira Coupling of 1-Chloroisoquinolines in the Formation of 1-Alkynyl-3-Substituted Isoquinolines,”Tetrahedron Letters, 52, no. 20 (2011): 2566–70.
  • K. Prabakaran, P. Manivel, and F. Nawaz Khan, “An Effective BINAP and Microwave Accelerated Palladium-Catalyzed Amination of 1-Chloroisoquinolines in the Synthesis of New 1,3-Disubstituted Isoquinolines,”Tetrahedron Letters, 51, no. 33 (2010): 4340–3.
  • C. Dasaradhan, Y. S. Kumar, F. Nawaz Khan, E. D. Jeong, and E. H. Chung, “Efficient Copper-Free Pd(OAc)2/Ruphos-Catalyzed Sonogashira Coupling in the Preparation of 3′-hydroxycorfin and gymnopalynes A analogues,”Tetrahedron Letters, 56, no. 1 (2015): 187–91.
  • C. Dasaradhan, Y. S. Kumar, K. Prabakaran, F. Nawaz Khan, E. D. Jeong, and E. H. Chung, “Efficient and Convenient Copper-Free Pd(OAc)2/Ruphos-Catalyzed Sonogashira Coupling in the Preparation of Corfin Analogues,”Tetrahedron Letters, 56, no. 6 (2015): 784–8.
  • Y. S. Kumar, C. Dasaradhan, K. Prabakaran, P. Manivel, F. Nawaz Khan, E. D. Jeong, and E. H. Chung, “Palladium Catalyzed Suzuki Miyaura Cross Coupling of 3-Chloroisochromen-1-One: synthesis of Glomellin and Reticulol Analogues,”Tetrahedron Letters, 56, no. 7 (2015): 941–5.
  • N. T. Patil, F. Nawaz Khan, and Y. Yamamoto, “Microwave-Enhanced Pd(0)/Acetic Acid Catalyzed Allylation Reactions of C, N, and O-Pronucleophiles with Alkynes,”Tetrahedron Letters, 45, no. 46 (2004): 8497–9.
  • Y. Isogai, F. Nawaz Khan, and N. Asao, CuX2-mediated [4+2] benzannulation as a new synthetic tool for stereoselective construction of haloaromatic compounds", Tetrahedron 65, no. 46 (2009): 9575-9582.
  • K. Prabakaran, F. Nawaz Khan, and J. S. Jin, “Ligand-Free, PdCl2(PPh3)2 Catalyzed, Microwave-Assisted Suzuki Coupling of 1-Chloro-3-Phenylisoquinoline in the Synthesis of Diversified 1,3-Disubstituted Isoquinolines,”Research on Chemical Intermediates 38, no. 2 (2012): 337–46.
  • S. S. Tajudeen, and F. Nawaz Khan, “Synthesis of Some 3‐Substituted Isochromen‐1‐Ones,” Synthetic Communications, 37, no. 20 (2007): 3649–56.
  • V. R. Hathwar, P. Manivel, F. N. Khan, and T. N. G. Row, “Evaluation of Intermolecular Interactions in Thioisocoumarin Derivatives: The Role of the Sulfur Atom in Generating Packing Motifs,”CrystEngComm 11, no. 2 (2009): 284–91.
  • P. Manivel, S. M. Roopan, D. P. Kumar, and F. N. Khan, “Isocoumarin Thioanalogues as Potential Antibacterial Agents,”Phosphorus, Sulfur, and Silicon 184, no. 10 (2009): 2576–82.
  • Milena Simic, Nikola Paunovic, Ivan Boric, Jelena Randjelovic, Sandra Vojnovic, Jasmina Nikodinovic-Runic, Marina Pekmezovic, and Vladimir Savic, “Functionalised Isocoumarins as Antifungal Compounds: Synthesis and Biological Studies,”Bioorganic & Medicinal Chemistry Letters 26, no. 1 (2016): 235–9.
  • Y.-H. Zhao, M.-J. Luo, H.-W. Liu, and L.-H. Wu, “K 2 CO 3 -Promoted Domino Reactions for Synthesis of Isocoumarins under Microwave Irradiation,” Synthetic Communications, 45, no. 7 (2015): 857–62.
  • G. Zhao, L.-Z. Yuan, M. Roudier, J.-F. Peyrat, A. Hamze, J.-D. Brion, O. Provot, and M. Alami, “A Convenient Metal-Free Synthesis of (E)-3-Styrylisocoumarins through Annulation of (E)-1,4-Diarylenynes,”Synthesis 48, no. 19 (2016): 3382–92.
  • A. Saeed, H. Rafique, and Z. Ashraf, “Synthesis and Antibacterial Evaluation of Typharin Analog: 6,8-Dihydroxy-7-Methyl-3-Styryl-3,4-Dihydroisocoumarin,”Journal of Asian Natural Products Research 15, no. 2 (2013): 130–5.
  • D. R. Nadkarni, and R. N. Usgaonkar, "Convenient syntheses of naturally occurring 3-propylisocoumarin and 3-propyl-1(2H)-isoquinolone and other related compounds", Indian Journal Chemistry, 17B, no. 6 (1979): 624–6.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.