10.1002/ejoc.201901660
European Journal of Organic Chemistry
COMMUNICATION
[8]
For key references in boron-catalysed amide synthesis see: a) K.
Ishihara, S. Ohara, H. Yamamoto, J. Org. Chem. 1996, 61, 4196–4197.
b) R. M. Al Zoubi, O. Marion, Hall, D. G. Angew. Chem. Int. Ed. 2008, 47,
2876–2879. c) N. Gernigon, R. M. Al Zoubi, D. G. Hall, J. Org. Chem.
2012, 77, 8386–8400. d) E. K. W. Tam, Rita, L. Y. Liu, A. Chen, Eur. J.
Org. Chem. 2015, 5, 1100–1107. e) T. Mohy El Dine, W. Erb, Y. Berhault,
J. Rouden, J. Blanchet, J. Org. Chem. 2015, 80, 4532–4544. f) T. Mohy
El Dine, J. Rouden, J. Blanchet, Chem. Commun. 2015, 51, 16084–
16087. g) H. Noda, M. Furutachi, Y. Asada, N. Kumagai, M. Shibasaki,
Nature Chem. 2017, 9, 571–577. h) C. R. Opie, H. Noda, M. Shibasaki,
N. Kumagai, Chem. Eur. J. 2019, 25, 4648–4653. i) H. Noda, Y. Asada,
M. Shibasaki, N. Kumagai, J. Am. Chem. Soc. 2019, 141, 1546–1554. j)
Z. Liu, H. Noda, M. Shibasaki, N. Kumagai, Org. Lett. 2018, 20, 612–615.
k) D. N. Sawant, D. B. Bagal, S. Ogawa, K. Selvam, S. Saito, Org. Lett.
2018, 20, 4397–4400. l) N. Shimada, M. Hirata, M. Koshizuka, N. Ohse,
R. Kaito, K. Makino, Org. Lett. 2019, 21, 4303–4308. m) M. T. Sabatini,
L. T. Boulton, T. D. Sheppard, Sci. Adv. 2017, 3, e1701028.
[9]
L. Hu, S. Xu, Z. Zhao, Y. Yang, Z. Peng, M. Yang, C. Wang, J. Zhao, J.
Am. Chem. Soc. 2016, 138, 13135–13138.
[10] a) T.-H. Chan, L. T. L. Wong, J. Org. Chem. 1969, 34, 2766–2767. b)
T.-H. Chan, L. T. L. Wong, J. Org. Chem. 1971, 36, 850–853. c) S. H.
Van Leeuwen, P. J. L. M. Quaedflieg, Q. B. Broxterman, R. M. J.
Liskamp, Tetrahedron Lett. 2002, 43, 9203–9207. d) T. Tozawa, Y.
Yamane, T. Mukaiyama, Chem. Lett. 2005, 34, 1586–1587. e) T. Tozawa,
Y. Yamane, T. Mukaiyama, Chem. Lett. 2005, 34, 734–735. f) T. Tozawa,
Y. Yamane, T. Mukaiyama, Chem. Lett. 2005, 34, 1334–1335. g) T.
Tozawa, Y. Yamane, T. Mukaiyama, Heterocycles 2006, 67, 629–641.
h) S. J. Aspin, S. Taillemaud, P. Cyr, A. B. Charette, Angew. Chem. Int.
Ed. 2016, 55, 13833–13837.
[11] D. C. Braddock, P. D. Lickiss, B. C. Rowley, D. Pugh, T. Purnomo, G.
Santhakumar, J. F. Fussell, Org. Lett. 2018, 20, 950–953.
[12] Z. Ruan, R. M. Lawrence, C. B. Cooper, Tetrahedron Lett. 2006, 47,
7649–7651. The title « Phenylsilane as an active amidation reagent for
the preparation of carboxamides and peptides » is misleading since no
peptide synthesis is reported there (following IUPAC peptide definition
as “amides derived from two or more amino carboxylic acid molecules”).
[13] Typically, 10 equiv of amines and 20 equiv of PhSiH3 were used.
[14] M. Sayes, A. B. Charette, Green Chem. 2017, 19, 5060–5064.
[15] M. D. Visco, J. M. Wieting, A. E. Mattson, Org. Lett. 2016, 18, 2883–2885.
[16] I. Shiina, H. Ushiyama, Y. Yamada, Y. Kawakita, K. Nakata, Chem. Asian
J. 2008, 3, 454–461.
[17] B. Iorga, J.-M. Campagne, Synlett 2004, 10, 1826–1828.
[18] a) J. I. Levin, E. Turos, S. M. Weinreb, Synth. Commun. 2006, 12, 989–
993. b) I. Maugras, J. Ponchet, P. Jouin, Tetrahedron 1990, 46, 2807–
2816. c) P. A. Jacobi, W. Zheng, Tetrahedron Lett. 1991, 32, 1279–1282.
[19] a) Y. Y. Jiang, L. Zhu, Y. Liang, X. Man, S. Bi, J. Org. Chem. 2017, 82,
9087–9096. b) B. Hu, Y.-Y. Jiang, P. Liu, R.-X. Zhang, Q. Zhang, T.-T.
Liu, S. Bi, Org. Biomol. Chem. 2019, 17, 9232–9242.
[20] a) K. G. Andrews, R. M. Denton, Chem. Commun. 2017, 53, 7982–7985.
A more recent NMR study concluded that amide synthesis did not directly
involve monoester 9 or 10. see b) P. B. White, S. J. Rijpkema, R. P.
Bunschoten, J. Mecinović, Org. Lett. 2019, 21, 1011–1014.
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