Development of Heterogeneous Rh Catalysts for Asymmetric Arylation Reactions

(1)

Kobayashi, S. Chem. - An Asian J. 2016, 11, 425.

(2)

Pugin, B.; Blaser, H. U. Top. Catal. 2010, 53, 953.

(3)

Masuda, K.; Ichitsuka, T.; Koumura, N.; Sato, K.; Kobayashi, S. Tetrahedron 2018, 74 (15),

1705–1730.

(4)

Mandoli, A.; Orlandi, S.; Pini, D.; Salvadori, P. Tetrahedron Asymmetry 2004, 15 (20), 3233–

3244.

(5)

Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verdugo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.;

Martínez-Merino, V.; Mayoral, J. A. Org. Lett. 2002, 4 (22), 3927–3930.

(6)

Cornejo, A.; Fraile, J. M.; García, J. I.; Gil, M. J.; Luis, S. V.; Martínez-Merino, V.; Mayoral, J.

A. J. Org. Chem. 2005, 70 (14), 5536–5544.

(7)

Burguete, M. I.; Cornejo, A.; García-Verdugo, E.; Gil, M. J.; Luis, S. V.; Mayoral, J. A.;

Martínez-Merino, V.; Sokolova, M. J. Org. Chem. 2007, 72 (12), 4344–4350.

(8)

Burguete, M. I.; Cornejo, A.; García-Verdugo, E.; García, J.; Gil, M. J.; Luis, S. V.; MartínezMerino, V.; Mayoral, J. A.; Sokolova, M. Green Chem. 2007, 9 (10), 1091.

(9)

Aranda, C.; Cornejo, A.; Fraile, J. M.; García-Verdugo, E.; Gil, M. J.; Luis, S. V.; Mayoral, J. A.;

Martínez-Merino, V.; Ochoa, Z. Green Chem. 2011, 13 (4), 983.

(10)

Lim, J.; Riduan, S. N.; Su, S. L.; Ying, J. Y. Adv. Synth. Catal. 2008, 350 (9), 1295–1308.

(11)

Castano, B.; Gallo, E.; Cole-Hamilton, D. J.; Dal Santo, V.; Psaro, R.; Caselli, A. Green Chem.

2014, 16 (6), 3202–3209.

(12)

Lundgren, S.; Ihre, H.; Moberg, C. Arkivoc 2008, 2008 (6), 73–80.

(13)

Seayad, A. M.; Ramalingam, B.; Yoshinaga, K.; Nagata, T.; Chai, C. L. L. Org. Lett. 2010, 12,

264.

(14)

Ramalingam, B.; Seayad, A. M.; Chuanzhao, L.; Garland, M.; Yoshinaga, K.; Wadamoto, M.;

Nagata, T.; Chai, C. L. L. Adv. Synth. Catal. 2010, 352, 2153.

(15)

Seayad, A. M.; Ramalingam, B.; Chai, C. L. L.; Li, C.; Garland, M. V.; Yoshinaga, K. Chem. - A

Eur. J. 2012, 18 (18), 5693–5700.

(16)

Takeda, K.; Oohara, T.; Shimada, N.; Nambu, H.; Hashimoto, S. Chem. - A Eur. J. 2011, 17 (50),

13992–13998.

(17)

Nitabaru, T.; Kumagai, N.; Shibasaki, M. Tetrahedron Lett. 2008, 49 (2), 272–276.

(18)

Nitabaru, T.; Nojiri, A.; Kobayashi, M.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131

(38), 13860–13869.

(19)

Ogawa, T.; Kumagai, N.; Shibasaki, M. Angew. Chemie - Int. Ed. 2013, 52 (24), 6196–6201.

(20)

Sureshkumar, D.; Hashimoto, K.; Kumagai, N.; Shibasaki, M. J. Org. Chem. 2013, 78 (22),

11494–11500.

(21)

Hashimoto, K.; Kumagai, N.; Shibasaki, M. Org. Lett. 2014, 16 (13), 3496–3499.

40

(22)

Hashimoto, K.; Kumagai, N.; Shibasaki, M. Chem. - A Eur. J. 2015, 21 (11), 4262–4266.

(23)

Bonfils, F.; Cazaux, I.; Hodge, P.; Caze, C. Org. Biomol. Chem. 2006, 4 (3), 493–497.

(24)

Ötvös, S. B.; Mándity, I. M.; Fülöp, F. ChemSusChem 2012, 5 (2), 266–269.

(25)

Arakawa, Y.; Wennemers, H. ChemSusChem 2013, 6 (2), 242–245.

(26)

Tsubogo, T.; Yamashita, Y.; Kobayashi, S. Chem. - A Eur. J. 2012, 18 (43), 13624–13628.

(27)

Tsubogo, T.; Oyamada, H.; Kobayashi, S. Nature 2015, 520, 329–332.

(28)

Hübner, S.; De Vries, J. G.; Farina, V. Adv. Synth. Catal. 2016, 358, 3.

(29)

Bryan, M. C.; Dunn, P. J.; Entwistle, D.; Gallou, F.; Koenig, S. G.; Hayler, J. D.; Hickey, M. R.;

Hughes, S.; Kopach, M. E.; Moine, G.; Richardson, P.; Roschangar, F.; Steven, A.; Weiberth, F.

J. Green Chem. 2018, 20, 5082.

(30)

Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron Asymmetry

1999, 10, 4047–4056.

(31)

Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125 (38), 11508–

11509.

(32)

Edwards, H. J.; Hargrave, J. D.; Penrose, S. D.; Frost, C. G. Chem. Soc. Rev. 2010, 39 (6), 2093.

(33)

Otomaru, Y.; Senda, T.; Hayashi, T. Org. Lett. 2004, 6 (19), 3357–3359.

(34)

Jana, R.; Tunge, J. A. Org. Lett. 2009, 11 (4), 971–974.

(35)

Jana, R.; Tunge, J. A. J. Org. Chem. 2011, 76 (20), 8376–8385.

(36)

Lipshutz, B. H.; Isley, N. A.; Moser, R.; Ghorai, S.; Leuser, H.; Taft, B. R. Adv. Synth. Catal.

2012, 354 (17), 3175–3179.

(37)

Sawano, T.; Ji, P.; McIsaac, A. R.; Lin, Z.; Abney, C. W.; Lin, W. Chem. Sci. 2015, 6, 7163–

7168.

(38)

Shen, G.; Osako, T.; Nagaosa, M.; Uozumi, Y. J. Org. Chem. 2018, 83, 7380.

(39)

Yasukawa, T.; Suzuki, A.; Miyamura, H.; Nishino, K.; Kobayashi, S. J. Am. Chem. Soc. 2015,

137, 6616–6623.

(40)

Kuremoto, T. Master Course Thesis, 2018.

(41)

Kuremoto, T.; Yasukawa, T.; Kobayashi, S. Adv. Synth. Catal. 2019, 361, 3698.

(42)

Wang, Z. Q.; Feng, C. G.; Zhang, S. S.; Xu, M. H.; Lin, G. Q. Angew. Chemie - Int. Ed. 2010, 49,

5780.

(43)

Fang, J. H.; Jian, J. H.; Chang, H. C.; Kuo, T. S.; Lee, W. Z.; Wu, P. Y.; Wu, H. L. Chem. - A

Eur. J. 2017, 23, 1830.

(44)

Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem.

Soc. 2004, 126, 13584.

(45)

Marques, C. S.; Burke, A. J. ChemCatChem 2011, 3, 635.

(46)

Kina, A.; Iwamura, H.; Hayashi, T. J. Am. Chem. Soc. 2006, 128 (12), 3904–3905.

(47)

Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.

41

(48)

Grubbs, R. H.; Kroll, L. R. C. J. Am. Chem. Soc. 1971, 93, 3062.

(49)

Grubbs, R. H.; Kroll, L. C.; Sweet, E. M. J. Macromol. Sci. Part A - Chem. 1973, 7, 1047.

(50)

M.Čapka; P.Svoboda; M.Černý; J.Hetflejš. Tetrahedron Lett. 1971, 12 (50).

(51)

Coliman, J. P.; Hegedus, L. S.; Cooke, M. P.; Norton, J. R.; Dolcetti, G.; Marquardt, D. N. J. Am.

Chem. Soc. 1972, 94, 1789.

(52)

Sussman, S. Ind. Eng. Chem. 1946, 38, 1228.

(53)

Bayer, E.; Eckstein, H.; Hagele, K.; König, W. A.; Brüning, W.; Hagenmaier, H.; Parr, W. J. Am.

Chem. Soc. 1970, 92, 1735.

(54)

Bayer, E.; Jung, G.; Halász, I.; Sebestian, I. Tetrahedron Lett. 1970, 11, 4503.

(55)

Mutter, M.; Hagenmaier, D. D. H.; Bayer, E. Angew. Chemie - Int. Ed. 1971, 10, 811.

(56)

Bayer, E.; M., M. Nature 1972, 237, 512.

(57)

Mutter, M.; Bayer, E. Angew. Chemie Int. Ed. English 1974, 13, 88.

(58)

Bayer, E.; Mutter, M.; Uhmann, R.; Polster, J.; Mauser, H. J. Am. Chem. Soc. 1974, 96, 7333.

(59)

H.Köster. Tetrahedron Lett. 1972, 13 (16), 1527.

(60)

H.Köster; K.Heyns. Tetrahedron Lett. 1972, 13 (16), 1531–1534.

(61)

H.Köster. Tetrahedron Lett. 1972, 13 (16), 1534.

(62)

Chapman, T. M.; Kleid, D. G. J. Chem. Soc. Chem. Commun. 1973, 193.

(63)

Atherton, E.; Clive, D. L. J.; Sheppard, R. C. J. Am. Chem. Soc. 1975, 97, 6584.

(64)

Gait, M. J.; Sheppard, R. C. J. Am. Chem. Soc. 1976, 98, 8514.

(65)

Arshady, R.; Atherton, E.; Gait, M. J.; Lee, K.; Sheppard, R. C. J. Chem. Soc. Chem. Commun.

1979, 423.

(66)

Atherton, E.; Brown, E.; Sheppard, R. C.; Rosevear, A. J. Chem. Soc. Chem. Commun. 1981,

1151.

(67)

Sparrow, J. T. J. Org. Chem. 1976, 41, 1350.

(68)

Becker, H.; Lucas, H.; Maul, J.; Pillai, V. N. R.; Anzinger, H.; Mutter, M. Die Makromol.

Chemie, Rapid Commun. 1982, 3, 217.

(69)

Hellermann, H.; Lucas, H.; Maul, J.; Pillai, V. N. R.; Mutter, M. Die Makromol. Chemie 1983,

184, 2603.

(70)

Bayer, E. Angew. Chemie - Int. Ed. 1991, 30 (2), 113–129.

(71)

Gooding, O. W.; Baudart, S.; Deegan, T. L.; Heisler, K.; Labadie, J. W.; Newcomb, W. S.; Porco,

J. A.; Van Eikeren, P. J. Comb. Chem. 1999, 1, 113.

(72)

Howard Adams, J.; Cook, R. M.; Hudson, D.; Jammalamadaka, V.; Lyttle, M. H.; Songster, M. F.

J. Org. Chem. 1998, 63, 3706.

(73)

Meldal, M. Tetrahedron Lett. 1992, 33 (21), 3077–3080.

(74)

Auzanneau, F. ‐I; Meldal, M.; Bock, K. J. Pept. Sci. 1995, 1 (1), 31–44.

(75)

Renil, M.; Meldal, M. Tetrahedron Lett. 1996, 37 (34), 6185–6188.

42

(76)

Rademann, J.; Grøtli, M.; Meldal, M.; Bock, K. J. Am. Chem. Soc. 1999, 121 (23), 5459–5466.

(77)

Kempe, M.; Barany, G. J. Am. Chem. Soc. 1996, 118 (30), 7083–7093.

(78)

Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40 (35), 6329–6332.

(79)

Liu, G.; Toy, P. H.; Malikayil, J. A.; Garibay, P.; Janda, K. D.; Garno, J. C.; Reger, T. S. J.

Comb. Chem. 2001, 3 (1), 117–124.

(80)

Mijalis, A. J.; Thomas, D. A.; Simon, M. D.; Adamo, A.; Beaumont, R.; Jensen, K. F.; Pentelute,

B. L. Nat. Chem. Biol. 2017, 13, 464.

(81)

Hartrampf, N.; Saebi, A.; Poskus, M.; Gates, Z. P.; Callahan, A. J.; Cowfer, A. E.; Hanna, S.;

Antilla, S.; Schissel, C. K.; Quartararo, A. J.; Ye, X.; Mijalis, A. J.; Simon, M. D.; Loas, A.; Liu,

S.; Jessen, C.; Nielsen, T. E.; Pentelute, B. L. Science (80-. ). 2020, 987, 980.

(82)

Côté, S. AMPHIPHILE SOLID SUPPORT FOR PEPTIDE SYNTHESIS, BIOORGANIC AND

ORGANIC CHEMISTRY, 2002, WO2002040559.

(83)

Côté, S. NEW POLYETHER BASED MONOMERS AND HIGHLY CROSS-LINKED

AMPHIPHILE RESINS, 2005, WO2005012277.

(84)

García-Martín, F.; Quintanar-Audelo, M.; García-Ramos, Y.; Cruz, L. J.; Gravel, C.; Furic, R.;

Côté, S.; Tulla-Puche, J.; Albericio, F. J. Comb. Chem. 2006, 8 (2), 213–220.

(85)

Cho, J. K.; Park, B. D.; Lee, Y. S. Tetrahedron Lett. 2000, 41, 7481.

(86)

Cho, J. K.; Park, B. D.; Park, K. B.; Lee, Y. S. Macromol. Chem. Phys. 2002, 203, 2211.

(87)

Kim, H.; Jin, K. C.; Chung, W. J.; Lee, Y. S. Org. Lett. 2004, 6, 3273.

(88)

Lee, T. K.; Ryoo, S. J.; Byun, J. W.; Lee, S. M.; Lee, Y. S. J. Comb. Chem. 2005, 7, 170.

(89)

Lee, T. K.; Lee, S. M.; Ryoo, S. J.; Byun, J. W.; Lee, Y. S. Tetrahedron Lett. 2005, 46, 7135.

(90)

Lee, T.; Choi, J.; Ryoo, S.; Lee, Y. S. J. Pept. Sci. 2007, 13, 655.

(91)

Choi, J. H.; Lee, T. K.; Byun, J. W.; Lee, Y. S. Tetrahedron Lett. 2009, 50, 4272.

(92)

Liu, R.; Marik, J.; Lam, K. S. J. Am. Chem. Soc. 2002, 124, 7678.

(93)

Cho, H. J.; Lee, T. K.; Kim, J. W.; Lee, S. M.; Lee, Y. S. J. Org. Chem. 2012, 77, 9156.

(94)

Kim, J.; Kim, S.; Shin, D. S.; Lee, Y. S. J. Pept. Sci. 2018, 24, 1.

(95)

Kim, J. H.; Jun, B. H.; Byun, J. W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 5827.

(96)

Kim, J. H.; Kim, J. W.; Shokouhimehr, M.; Lee, Y. S. J. Org. Chem. 2005, 70, 6714.

(97)

Shokouhimehr, M.; Kim, J. H.; Lee, Y. S. Synlett 2006, 618.

(98)

Kim, J. H.; Lee, D. H.; Jun, B. H.; Lee, Y. S. Tetrahedron Lett. 2007, 48, 7079.

(99)

Choi, B. G.; Song, R.; Nam, W.; Jeong, B. Chem. Commun. 2005, 2960.

(100)

Bo, G. C.; Ko, S. Y.; Nam, W.; Jeong, B. Bull. Korean Chem. Soc. 2005, 26, 1819.

(101)

Yamada, Y.; Qiao, K.; Bao, Q.; Tomida, D.; Nagao, D.; Konno, M.; Yokoyama, C. Catal.

Commun. 2009, 11, 227.

(102)

Sugimura, R.; Qiao, K.; Tomida, D.; Yokoyama, C. Catal. Commun. 2007, 8, 770.

(103)

Qiao, K.; Hagiwara, H.; Yokoyama, C. J. Mol. Catal. A Chem. 2006, 246, 65.

43

(104)

Haraguchi, N.; Nishiyama, A.; Itsuno, S. J. Polym. Sci. Part A Polym. Chem. 2010, 48 (15),

3340–3349.

(105)

Ullah, M. W.; Thao, N. T. P.; Sugimoto, T.; Haraguchi, N. Mol. Catal. 2019, 473 (April),

110392.

(106)

Ullah, M. W.; Haraguchi, N. Catalysts 2019, 9 (11), 960.

(107)

Li, X.; Chen, M.; Yang, B.; Zhang, S.; Jia, X.; Hu, Z. RSC Adv. 2014, 4 (82), 43278.

(108)

Li, X.; Yang, B.; Jia, X.; Chen, M.; Hu, Z. RSC Adv. 2015, 5, 89149.

(109)

Li, X.; Yang, B.; Zhang, S.; Jia, X.; Hu, Z. Colloid Polym. Sci. 2017, 295, 573.

(110)

Vaino, A. R.; Janda, K. D. J. Comb. Chem. 2000, 2, 579.

(111)

Bouillon, I.; Soural, M.; Miller, M. J.; Krchňák, V. J. Comb. Chem. 2009, 11, 213.

(112)

Li, Y.; Liu, B. ACS Macro Lett. 2017, 6, 1315.

(113)

Stöber, W.; Fink, A.; Bohn, E. Jounal Colloid Interface Sci. 1968, 26, 62.

(114)

Rostovtsev, V. V; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chemie - Int. Ed. 2002,

41, 2596.

(115)

Shao, C.; Wang, X.; Zhang, Q.; Luo, S.; Zhao, J.; Hu, Y. J. Org. Chem. 2011, 76, 6832.

(116)

Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853.

(117)

Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 15046.

(118)

Dommerholt, J.; Schmidt, S.; Temming, R.; Hendriks, L. J. A.; Rutjes, F. P. J. T.; Van Hest, J. C.

M.; Lefeber, D. J.; Friedl, P.; Van Delft, F. L. Angew. Chemie - Int. Ed. 2010, 49, 9422.

(119)

Gordon, C. G.; MacKey, J. L.; Jewett, J. C.; Sletten, E. M.; Houk, K. N.; Bertozzi, C. R. J. Am.

Chem. Soc. 2012, 134, 9199.

(120)

Yasukawa, T.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2012, 134, 16963–16966.

(121)

Yasukawa, T.; Saito, Y.; Miyamura, H.; Kobayashi, S. Angew. Chemie - Int. Ed. 2016, 55 (28),

8058–8061.

(122)

Miyamura, H.; Nishino, K.; Yasukawa, T.; Kobayashi, S. Chem. Sci. 2017, 8362–8372.

(123)

Yasukawa, T.; Kuremoto, T.; Miyamura, H.; Kobayashi, S. Org. Lett. 2016, 18 (11), 2716–2718.

44

Acknowledgements

I greatly thank Prof. Dr. Shū Kobayashi for allowing me to join his laboratory and giving me

wonderful opportunity and environment to study and practice synthetic organic chemistry.

I greatly thank Proj. Assoc. Prof. Dr. Tomohiro Yasukawa for his kind instructions, valuable

suggestions, enthusiastic discussions, and encouragement.

I greatly thank Mr. Ren Sadatsune for his contribution to part of Chapter 3.

I greatly thank Mr. Noriaki Kuramitsu and Dr. Tei Maki for STEM analysis.

I greatly thank Materials Education program for the future leaders in Research, Industry, and

Technology (MERIT) for financial supports and educations.

I also thank all the members of Synthetic Organic Chemistry Laboratory for various supports.

December 2020

Department of Chemistry,

School of Science,

The University of Tokyo

Tatsuya Kuremoto

45

...