A facile method for the carbonylative cyclization of o-bromobenzoic acid with primary amine using Pd(OAC)2 as a metal precursor and 1,1'-bis(diphenylphosphino)ferrocene (dppf) as a ligand has been developed. The effect of various reaction parameters such as ligand, solvent, base, time and temperature on this cyclization was studied. The optimized protocol was used for a wide variety of substituted aryl amines with different steric and electronic properties, affording the corresponding isoindoline-1,3-diones in good to excellent yields under atmospheric pressure of carbon monoxide at 100°C within 10 h using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a base. The reaction system finds attractive alternative to the conventional multistep synthetic process and thus represents an effective utilization of carbonylative protocol for synthesis of valuable chemicals.
. Facile synthesis of isoindoline-1,3-diones by palladium-catalyzed carbonylative cyclization of o-bromobenzoic acid and primary amines[J]. Frontiers of Chemical Science and Engineering, 2013, 7(2): 226-232.
Mayur V. KHEDKAR, Bhalchandra M. BHANAGE. Facile synthesis of isoindoline-1,3-diones by palladium-catalyzed carbonylative cyclization of o-bromobenzoic acid and primary amines. Front Chem Sci Eng, 2013, 7(2): 226-232.
Ashcroft A T, Cheetham A K, Green M L H, Vernon P D F. Partial oxidation of methane to synthesis gas using carbon dioxide. Nature , 1991, 352(6332): 225–226
2
Trost B M. The atom economy--a search for synthetic efficiency. Science , 1991, 254(5037): 1471–1477
3
Abramovitch R A, Shinkai I, Mavunkel B J, More K M, O'Connor S, Ooi G H, Pennington W T, Srinivasan P C, Stowers J R. New ring systems from 1,2-benzisothiazole-1,1-dioxides and related compounds. Tetrahedron , 1996, 52(9): 3339–3354
4
Wood J L, Stoltz B M, Goodman S N. Total Synthesis of (+)-RK-286c, (+)-MLR-52, (+)-staurosporine, and (+)-K252a. Journal of the American Chemical Society , 1996, 118(43): 10656–10657
5
Hall I H, Chapman J M Jr, Wong O T. The cytotoxic activity of cyclic imido alkyl ethers, thioethers, sulfoxides, sulfones and related derivatives. Anti-Cancer Drugs , 1994, 5(1): 75–82
6
Makonkawkeyoon S, Limson-Pobre R N R, Moreira A L, Schauf V, Kaplan G. Thalidomide inhibits the replication of human immunodeficiency virus type 1. Proceedings of the National Academy of Sciences of the United States of America , 1993, 90(13): 5974–5978
7
Figg W D, Raje S, Bauer K S, Tompkins A, Venzon D, Bergan R, Chen A, Hamilton M, Pluda J, Reed E. Pharmacokinetics of thalidomide in an elderly prostate cancer population. Journal of Pharmaceutical Sciences , 1999, 88(1): 121–125
8
Atra E, Sato E I. Treatment of the cutaneous lesions of systemic lupus erythematosus with thalidomide. Clinical and Experimental Rheumatology , 1993, 11(5): 487–493
9
Ochonisky S, Verroust J, Bastuji-Garin S, Gherardi R, Revuz J. Thalidomide neuropathy incidence and clinico-electrophysiologic findings in 42 patients. Archives of Dermatology , 1994, 130(1): 66–69
10
Miyachi H, Azuma A, Ogasawara A, Uchimura E, Watanabe N, Kobayashi Y, Kato F, Kato M, Hashimoto Y. Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity. Journal of Medicinal Chemistry , 1997, 40(18): 2858–2865
11
Li X, Zhan J, Li Y. Facile syntheses and characterization of hyperbranched poly(ester-amide)s from commercially available aliphatic carboxylic anhydride and multihydroxyl primary amine. Macromolecules , 2004, 37(20): 7584–7594
12
Hellwinkel D, Lenz R, L?mmerzahl F. Heterocyclic syntheses via carbanionically induced rearrangement reactions. Tetrahedron , 1983, 39(12): 2073–2084
13
Mori M, Chiba K, Ohta N, Ban Y. A novel synthesis of cyclic imides and quinolone by use of paliadium catalyzed carbonylation. Heterocycles , 1979, 13(1): 329–332
14
Perry R J, Turner S R. Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines. Journal of Organic Chemistry , 1991, 56(23): 6573–6579
15
Taká A, Acscs P, Kollar L. Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene. Tetrahedron , 2008, 64(6): 983–987
16
Worlikar S A, Larock R C. Palladium-catalyzed one-step synthesis of isoindole-1,3-diones by carbonylative cyclization of o-halobenzoates and primary amines. Journal of Organic Chemistry , 2008, 73(18): 7175–7180
17
Khedkar M V, Khan S R, Sawant D N, Bagal D B, Bhanage B M. Palladium on carbon: an efficient, heterogeneous and reusable catalytic system for carbonylative synthesis of N-substituted phthalimides. Advanced Synthesis & Catalysis , 2011, 353(18): 3415–3422
18
Khedkar M V, Khan S R, Dhake K P, Bhanage B M. Carbonylative cyclization of o-halobenzoic acids for synthesis of N-substituted phthalimides using polymer supported palladium N-heterocyclic carbene as an efficient, heterogeneous and reusable catalyst. Synthesis , 2012, 44(16): 2623–2629
19
Cao H, Alper H. Palladium-catalyzed double carbonylation reactions of o-dihaloarenes with amines in phosphonium salt ionic liquids. Organic Letters , 2010, 12(18): 4126–4129
20
Khedkar M V, Tambade P J, Qureshi Z S, Bhanage B M. Pd/C: an efficient, heterogeneous and reusable catalyst for phosphane-free carbonylative suzuki coupling reactions of aryl and heteroaryl iodides. European Journal of Organic Chemistry , 2010, 2010(36): 6981–6986
21
Gadge S T, Khedkar M V, Lanke S R, Bhanage B M. Oxidative aminocarbonylation of terminal alkynes for the synthesis of alk-2-ynamides by using palladium-on-carbon as efficient, heterogeneous, phosphine-free, and reusable catalyst. Advanced Synthesis & Catalysis , 2012, 354(10): 2049–2056
22
Khedkar M V, Sasaki T, Bhanage B M. Immobilized palladium metal containing ionic liquid catalyzed alkoxycarbonylation, phenoxycarbonylation and aminocarbonylation reactions. ACS Catalysis , 2013: 287–293
23
Qureshi Z S, Revankar S A, Khedkar M V, Bhanage B M. Aminocarbonylation of aryl iodides with primary and secondary amines in aqueous medium using polymer supported palladium-N-heterocyclic carbene complex as an efficient and heterogeneous recyclable catalyst. Catalysis Today , 2012, 198(1): 148–153
