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RSC Advances
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DOI: 10.1039/C5RA18820B
ARTICLE
Journal Name
12 A. Pelter, K. Smith and H. C. Brown, Borane Reagents,
Academic Press, London, 1998; K. Smith, “Organoboron
Chemistry”. In Organometallic in Synthesis, Ed. M. Schlosser,
Wilet Chinchester, 1994.
13 Boron, Metallo-Boron, Compounds and Boranes Ed. Adams,
and R. M. Wiley, New York, 1964, p.693. data quoted in
Registry of Toxic Effect of Chemicals Substances, NIOSH,
Acknowledgements
Acknowledgements RHT thanks department of Science and
Technology (DST) Ministry of Science, India for financial
support of this project (SR/FT/CS-85/2011), GVB and TGK
thank UGC India, for Rajiv Gandhi National Fellowship.
2002
.
14 a) D. G. Hall, Boronic Acids: Preparation, Applications in
Organic Synthesis and Medicine; Wiley-VCH: Weinheim,
2011, and references cited therein; b) D. G. Hall, Boronic
Acids: Preparation and Applications in Organic Synthesis,
Medicine and Materials (Second Edition) Wiley-VCH:
Weinheim, 2011, and references cited therein.; c) Y. Guan
and Y. Zhang, Chem. Soc. Rev., 2013,42, 8106; d) J. N.
Cambre and B. S. Sumerlin, Polymer 2011, 52, 4631.
15 For metal catalyzed borylation reactions: See a) W. K. Chow,
Y. O. Yuen, P. Y. Choy, C. M. So, C. P. Lau, K. W. Wong and F.
Y. Kwong, R. S. Advances, 2013, 3, 12518-12539; b) T.
Ishiyama, M. Murata and N. Miyura, J. Org. Chem., 1995, 60,
7508-7510; c) A. L. S. Thomson, G. Kabalka, M. R. Akula and
Huffman, Synthesis, 2005, 547-550; d) A. Molander, L. N.
Cavalcanti and C. Garcia-Garcia,J. Org. Chem., 2013, 78,
6427-6439; e) G. A. Molander, S. L. J. Trice and S. M.
Kennedy, Org. Chem. 2012, 77, 8678-8688; f) W. Tang, S.
Keshipeddy, Y. Zhang, X. Wei, J. Savoie, N. D. Patel, N. K. Yee
and C. H. Senanayake, Org. Lett, 2011, 13, 1366-1369; g) S.
Dundik and G. C. Fu, J. Am. Chem. Soc., 2012, 134, 10693-
10697; h) J. Takagi, A. Kamon, T. Ishiyama and N. Miyaura
Synlett, 2002, 1880-1882; i) J. Takagi, K. Takahashi, T.
Ishiyama and N. Miaura, J. Am. Chem. Soc. 2002, 124, 8001-
8006; j) D. G. Hall, Boronic Acids: Preparation, Applications in
Organic Synthesis and Medicine; Wiley-VCH: Weinheim,
2011, and references cited therein.
Notes and references
1
a) Metal catalyzed cross coupling reactions (Eds.: F.
Diederich, and P. J. Stang, Wiley-VCH: Weinheim. 1997); b)
Palladium-Catalyzed Cross-Coupling: A Historical Contextual
Perspective to the 2010 Nobel Prize J. Seechurn, C. C. Carin,
M. O. Kitching, T. J. Colacot, and V. Snieckus, Angewandte
Chemie International Edition, 2012, 51, 5062; c) Palladium
Catalysed Cross Coupling Reactions of Organoborn
Compounds. N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95,
2457.
2
a) T. Wirth, M. Ochiai, A. Varvgolis, V. V. Zhdankin, G. F.
Koser, H. Tohma and Y. Kita, Topics in Current Chemisty:
Hypervalent Iodine Chemisrty-/- Modern Developments in
Organic Synthesis, pp 1-248, Springer-Verlag, Berlin, 2002; b)
A. Varvoglis, Hypervalent Iodine in Organic Synthesis, pp. 1-
223, Academic Press, London, 1997; c) P. Stang and V. V.
Zhadankin, Chem. Rev. 1996, 96, 1123; d) A. Parra and S.
Reboredo, Chem.- A. Eur. J., 2013, 19, 17244.
3
4
S. W. Kim, J. H. Park, S. D. Yang, M. G. Hur, Y. -S. Kim, J. -S.
Chai, Y. S. Kim and K. H. Yu, Bull. Korean Chem. Soc., 2004,
25, 1147-1150.
a) M. K. Dewanjee, Radioiodination : Theory, Practice and
Biomedical Applications; Kluwer Academic Publishers:
Bosten, 1992, pp; b) R. Weissleder, Science 2006, 312, 1168-
1171.
16 For borylation of arenes via C-H activation See: a) J. M.
Murphy, X. Liao and J. F. Hartwig, J. Am. Chem. Soc., 2007,
5
6
J. March, Advance Organic Chemistry; Wiley-Interscience:
New York, 2000, 4th ed.
a) J. Iskra, S. Stavber and M. Zupan, Synthesis, 2004, 1869-
1873; b) N. C. Ganguly, S. K. Barik and S. Dutta, Synthesis,
2010, 1467-1472; c) K. M. Sosnowski and L. Skulski,
129, 15434-15435 b) B. Partridge and J. F. Hartwig, Org. Lett.,
2013, 15, 140-143; c) S. Sebelius, J. Olsson and K. J. Szabo, J.
Am. Chem Soc. 2005, 127, 10478; c) V. J. Olsson and K.
J.Szabo, Angew. Chem. Int. Ed. 2007, 46, 689; e) V. J. Olsson,
S. Sebelius, N. Selander and K. J. Szabo, J. Am. Chem. Soc.,
2006, 128, 4588; f) V. J. Olsson and K. J. Szabo, Org. Lett.
2008, 10, 3129; g) D. Hall, Boronic Acids: Preparation,
Applications in Organic Synthesis and Medicine; Wiley-VCH:
Weinheim, 2011, and references cited therein; h) M. Murata,
S. Watanabe and Y. Masuda, J. Org. Chem., 1997, 62, 6458; i)
M. Murata, T. Oyama, S. Watanabe and Y. Masuda,J. Org.
Chem. 2000, 65, 164; j) C. Kleeberg, L. Dang, Z. Lin and T. B.
Marder, Angew. Chem. Int. Ed. 2009, 48, 5350.
Synthesis, 2006, 1195-1199; d) A.-S. Castanet, F. Colobert
and P. -E. Broutin, Tetrahedron Lett. 2002, 43, 5047-5048; e)
P. Lulinski and L. Skulski, Bull. Chem. Soc. Jpn. 1997, 70, 1665;
f) P. Lulinski, A. Kryska, M. Sosnowski and L. Skulski,
Synthesis, 2004, 441-445; g) B. Krassowska-Swiebocka, P.
Lulinkski and L. Skulski, Synthesis. 1995, 926; h) H. O. Wirth,
O. Konigstein and W. Kern, Liebigs Ann.Chem. 1977, 42,
4049; i) S. Ahmed and S. Razaq, Tetrahedron 1976, 32, 503; j)
H. Suzuki, K. Nakamura and R. Goto, Bull. Chem. Soc. Jpn.
1966, 39, 128; k) H. Suzuki, Bull. Chem. Soc. Jpn. 1970, 43,
481; l) A. Shimizu, K. Yamataka and T. Isoya, Bull. Chem. Soc.
Jpn. 1985, 58, 1611; m) A. Bachki, F. Foabelo and M. Yus,
Tetrahedron 1994, 50, 5139; n) W.–W. Sy, B. A. Lodge and A.
W. By, Synth. Commun. 1990, 20, 877
17 a) C. -Z. Tao, X. Cui, A. -X. Liu, L. Liu and Q. -X. Guo,
Tetrahedron Lett. 2007, 48, 3525–3529; b) S. Mohammed, A.
K. Padala, A. Dar, B. Singh, B. Sreedhar, R. A. Vishwakarma
and S. B. Bharate, Tetrahedron, 2012, 68, 8156–8162.
18 A. Kar, I. A. Sayeed, W. F. Low, H. M. Kaiser, M. Beller and M.
K. Tse, Org Lett., 2007, 9, 3405.
19 a) S. Guo, L. Lu and H. Cai, Synlett, 2013, 24, 1712-1714; b) J.
Xu, X. Wang, C. Shao, D. Su, G. Cheng and Y. Hu, Org. Lett.,
2010, 12, 1964-1967; c) C. Zhu, R. Wang and J. R. Falck, Org.
Lett., 2012, 14, 3494-3497; d) G. A. Molander, L. N.
Cavalcanti, J. Org. Chem., 2011, 76, 623-630; e) A. Gogoi and
U. Bora, Synlett, 2012, 23, 1079-1081; f) H. -L. Qi, D. -S. Chen,
J. -S. Ye and J. -M. Huang, J. Org. Chem., 2013, 78, 7482-
7487; g) D. -S. Chen, J. –M. Huang, Synlett, 2013, 24, 499-
501; h) G. K. S. Prakash, S. Chacko, C. Panja, T. E. Thomas, L.
Gurung, G. Rasul, T. Mathew and G. A. Olah, Adv. Synth.
Catal., 2009, 351, 1567–1574.
7
8
T. Sandmeyer, Chem. Ber, 1884, 1633.
a) V. D. Filimonov, N. I. Semenischeva, E. A. Krasnokutskaya,
A. N. Tretyakov, H. Y. Hwang and K. –W. Chi, Synthesis, 2008
185-187; b) V. D. Filimonov and P. Knochel, Synthesis, 2007
,
,
81-84; c) A. Hubbard, T. Okazaki and K. K. Laali, J. Org. Chem.,
2008, 73, 316-319.
R. W. Fish and M. Rosenblum, J. Org. Chem. 1965, 1253.
9
10 A. McKillop, J. D. Hunt, M. J. Zelesko, J. S. Fowler, E. C. Taylor,
G. Mc-Gillivray and F. Kienzle, J. Am. Chem. Soc. 1971, 93,
484.
11 A. Klapars and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124,
14844-14845.
20 a) C. Thiebes, G. K. S. Prakash, N. A. Petasis and G. A. Olah,
Synlett, 1998, 141–142; b) L. Niu, H. Zhang, H. Yang and H.
8 | J. Name., 2012, 00, 1-3
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