Ir/Sn dual-reagent catalysis towards highly selective alkylation of arenes and heteroarenes with benzyl alcohols

Journal of Chemical Sciences

Volumn 120, Issue 5, 2008, Pages 429-439

  Sujit, R O Y ^a   Podder, Susmita ^a   Choudhury, Joyanta ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Alkylation; Benzyl alcohol; Bimetallic; Catalysis; Iridium; Organometallic; Tin

Indexed keywords

ALKYLATION; BENZYL ALCOHOL; BIMETALLIC; CATALYSIS; ORGANOMETALLIC; TIN;

CHEMICAL REACTIONS; HYDROCARBONS;

IRIDIUM;

EID: 53849100010     PISSN: 02534134     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-008-0068-2     Document Type: Article

References (94)

1. For reviews on Friedel-Crafts alkylation chemistry see: (a) Olah G A 1964 Friedel-Crafts and related reactions (New York: Wiley-Interscience) vol. II, Part 1;
2. (b) Olah G A, Krishnamurti R and Prakash G KS 1991 Friedel-Crafts alkylation in comprehensive organic synthesis (eds) B M Trost and I Fleming (Oxford: Pergamon Press);
3. (c) Roberts R M and Khalaf A A 1984 Friedel-Crafts alkylation chemistry. A century of discovery (New York: Marcel Dekker)
4. (a) Kobayashi S 1994 Synlett. 689;
5. (b) Kobayashi S 1995 J. Synth. Org. Chem. Jpn. 53 370;
6. (c) Sharma G V M and Mahalingam A K 1999 J. Org. Chem. 64 8943;
7. (d) Shiina I and Sujuki M 2002 Tetrahedron Lett. 43 6391;
8. (e) Mukaiyama T, Kamiyama H and Yamanaka H 2003 Chem. Lett. 32 814
9. (a) Fukuzawa S-I, Tsuchimoto T and Hiyama T 1997 J. Org. Chem. 62 151;
10. (b) Tsuchimoto T, Tobita K, Hiyama T and Fukuzawa S 1997 J. Org. Chem. 62 6997;
11. (c) Noji M, Ohno T, Fuji K, Futaba N, Tajima H and Ishii K 2003 J. Org. Chem. 68 9340
12. (a) Mertins K, Jovel I, Kischel J, Zapf A and Beller M, Angew. Chem. Int. Ed. 2005 44 238;
13. (b) Iovel I, Mertins K, Kischel J, Zapf A and Beller M 2005 Angew. Chem. Int. Ed. 44 3913;
14. (c) Mertins K, Iovel I, Kischel J, Zapf A and Beller M 2006 Adv. Synth. Catal. 348 691;
15. (d) Bandini M, Melloni A and Umani-Ronchi A 2004 Angew. Chem. Int. Ed. 43 550
16. For some heterogeneous examples see: (a) Yamamoto T, Hideshima C, Prakash G K S and Olah G A 1991 J. Org. Chem. 56 2089;
17. (b) Coq B, Gourves V and Figueras F 1993 Appl. Catal. A 100 69;
18. (c) Yadav G D, Thorat T S and Khumbar P S 1993 Tetrahedron Lett. 34 529;
19. (d) Cseri T, Bekassy S, Figueras F and Rinzer S 1995 J. Mol. Catal. A 98 101;
20. (e) da Silva M S M, da Costa C L, Pinto M M and Lachter E R 1995 React. Funct. Polym. 25 55;
21. (f) Morais M, Torres E F, Carmo LMPM, Pastura NMR, Gonzalez W A, dos Santos A C B and Lachter E R 1996 Catal. Today, 28 17;
22. (g) Zhou D-Q, Yang J-H, Dong G-M, Huang M-Y and Jiang Y-Y 2000 J. Mol. Catal. A 159 85;
23. (h) Deshpande A B, Bajpai A R and Samant S D 2001 Appl. Catal. A 209 229
24. (a) van den Beuken E K and Feringa B L 1998 Tetrahedron 54 12985;
25. (b) Shibasaki M 2000 in Stimulating concepts in chemistry (eds) F Vögtle, J F Stoddart and M Shibasaki (Weinheim: Wiley-VCH) pp 105-121;
26. (c) Wheatley N and Kalck P 1999 Chem. Rev. 99 3379;
27. (d) Fogg D E and dos Santos E N 2004 Coord. Chem. Rev. 248 2365;
28. (e) Kamijo S and Yamamoto Y 2004 in Multimetallic catalysts in organic synthesis (eds) M Shibasaki and Y Yamamoto (Weinheim: Wiley-VCH) pp 1-52;
29. (f) Ma J-A and Cahard D 2004 Angew. Chem. Int. Ed. 43 4566;
30. (g) Rowlands G J 2001 Tetrahedron 57 1865
31. Roy U K and Roy S 2007 Tetrahedron Lett. 48 7177
32. Roy U K, Jana P K and Roy S 2007 Tetrahedron Lett. 48 1183
33. Roy U K and Roy S 2006 Tetrahedron 62 678
34. Roy U K and Roy S 2006 J. Organomet. Chem. 691 1525
35. Banerjee M and Roy S 2006 J. Mol. Catal. A 246 231
36. Banerjee M, Roy U K, Sinha P and Roy S 2005 J. Organomet. Chem. 690 1422
37. Banerjee M and Roy S 2004 Org. Lett. 6 3137
38. Sinha P and Roy S 2004 Organometallics 23 67
39. Banerjee M and Roy S 2003 Chem. Commun. 534
40. Sinha P and Roy S 2001 Chem. Commun. 1798
41. Kundu A, Sinha P, Roy S, Prabhakar S, Vairamani M, Shankar A Ravi and Kunwar A C 2001 Organometallics 20 157
42. Kundu A and Roy S 2000 Organometallics 19 105
43. Kundu A, Prabhakar S, Vairamani M and Roy S 1999 Organometallics 18 2782
44. Kundu A, Prabhakar S, Vairamani M and Roy S 1997 Organometallics 16 4796
45. Choudhury J, Podder S and Roy S 2005 J. Am. Chem. Soc. 127 6162
46. Choudhury J, Kumar D K and Roy S 2007 J. Organomet. Chem. 692 5614
47. Podder S, Choudhury J and Roy S 2007 J. Org. Chem. 72 3129
48. Podder S and Roy S 2007 Tetrahedron 63 9146
49. Podder S, Choudhury J, Roy U K and Roy S 2007 J. Org. Chem. 72 3100
50. Choudhury J and Roy S 2008 J. Mol. Catal. A 279 37
51. Olah G A, Kobayashi S and Tashiro M 1972 J. Am. Chem. Soc. 94 7448
52. (a) Nordberg M G, Kolmodin K, Aquist J, Queener S F and Hallberg A 2001 J. Med. Chem. 44 2391;
53. (b) Sun H H, Paul V J and Fenical W 1983 Phytochemistry 22 743;
54. (c) Hoshina H, Maekawa K, Taie K, Igarashi T and Sakurai T 2003 Heterocycles 60 1779;
55. (d) Manzoni C, Lovati M R, Bonelli A, Galli G and Sirtori C R 1990 Eur. J. Pharmacol. 190 39;
56. (e) Rose C, Vtoraya O, Pluzanska A, Davidson N, Gershanovich M, Thomas R, Johnson S, Caicedo J J, Gervasio H, Manikhas J, Ayed F B, Radoux S B, Ross H A C and Lang R 2003 Eur. J. Cancer. 39 2318;
57. (f) Long Y-Q, Jiang X-H, Dayam R Sanchez T, Shoemaker R, Sei S and Neamati N 2004 J. Med. Chem. 47 2561;
58. (g) de Lang R-J, van Hooijdonk M J C M, Brandsma L, Kramer H and Seinen W 1998 Tetrahedron 54 2953
59. (a) Skabara P J, Serebryako I M and Perepichka I F 1999 Synth. Met. 102 1336;
60. (b) Khan M S, Al-Mandhary M R A, Al-Suti M K, Ahrens B, Mahon M F, Male L, Raithby P R, Boothby C E and Kohler A 2003 Dalton Trans. 74;
61. (c) Jacob J, Oldridge L, Zhang J Y, Gaal M, List E J W, Grimsdale A C and Müllen K 2004 Curr. Appl. Phys. 4 339
62. (a) Philp D and Stoddart J F 1996 Angew. Chem. Int. Ed. Engl. 35 1154;
63. (b) Conn M M and Rebek Jr J 1997 Chem. Rev. 97 1647;
64. (c) Jasat A and Sherman J C 1999 Chem. Rev. 99 931
65. (a) Berger N and Jay P 1986 IEEE Trans. Elect. Insul. EI-21 59;
66. (b) Atsushi S, Shigenobu K, Keiji E and Hideyuki D 1988 Eur. Pat. Appl. EP 262456
67. Kunio S, Takao T and Toshikatsu S 1997 Jpn. Kokai. Tokkyo Koho JP 09025202
68. Verevkin S P 1999 J. Chem. Eng. Data 44 175
69. Walter R, Kirchner S and Franz R 2002 US Patent 6,399,804
70. (a) Jin D, Hou Z, Luo Y and Zheng X 2006 J. Mol Catal A: Chemical 243 233;
71. (b) Petchmanee T, Ploypradith P and Ruchirawat S 2006 J. Org. Chem. 71 2892;
72. (c) Chandrasekhar S, Reddy C R and Babu B N 2002 J. Org. Chem. 67 9080;
73. (d) Inoh J-I, Satoh T, Pivsa-Art S, Miura M and Nomura M 1998 Tetrahedron Lett. 39 4673;
74. (e) Kodomari M and Taguchi S 1996 J. Chem. Res. Synopses 240;
75. (f) Mahindaratne M P D and Wimalasena K 1998 J. Org. Chem. 63 2858;
76. (g) Shi M, Okamoto Y and Takamuku S 1990 Bull. Chem. Soc. Japan 63 2731;
77. (h) Rueping M, Nachtsheim B J and Winai I 2006 Adv. Synth. Catal. 348 1033;
78. (i) Lee M J, Lee K Y, Park D Y and Kim J N 2006 Tetrahedron 62 3128;
79. (j) Choudhury J, Podder S and Roy S 2005 J. Am. Chem. Soc. 127 6162;
80. (k) De Lang R-J, Van H Marcel J C M, Brandsma L, Kramer H and Seinen W 1998 Tetrahedron 54 2953;
81. (l) Fukuzawa S-I, Tsuchimoto T and Hiyama T 1997 J. Org. Chem. 62 151;
82. (m) Tsuchimoto T, Hiyama T and Fukuzawa S-I 1996 Chem. Commun. 2345;
83. (n) Molander G A and Elia M D 2006 J. Org. Chem. 71 9198;
84. Flaherty A, Trunkfield A and Barton W 2005 Org. Lett. 7 4975;
85. (o) Eisch J J and Gitua J N 2007 Organometallics 26 778;
86. (p) Sefkow M and Buchs J 2003 Org. Lett. 5 193;
87. (q) Rottlaender M and Knochel P 1997 Tetrahedron Lett. 38 1749;
88. Blackwell J and Hickinbottom W J 1963 J. Chem. Soc. 366;
89. (r) Rueping M, Nachtsheim B J and Ieawsuwan W 2006 Adv. Syn. Catal. 348 1033;
90. (s) Shi M, Okamoto Y and Takamuku S 1990 Bull. Chem. Soc. Japan 63 2731;
91. (t) Hall S S and Farahat S E 1987 J Het. Chem. 24 1205;
92. (u) Gabriele B, Salerno G and Fazio A 2000 Org. Lett. 2 351;
93. (v) Ku Y-Y, Patel R R and Sawick D P 1996 Tetrahedron Lett. 37 1949;
94. (w) Avendano C, De Diego C and Elguero J 1990 Monatshefte fur Chemie 121 649