Reactions of substituted pyridines with electrophilic boranes

Caputo CB, Geier SJ, Winkelhaus D, Mitzel NW, Vukotic VN, Loeb SJ, Stephan DW (2012)
Dalton Transactions 41(7): 2131-2139.

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Abstract / Bemerkung
The lutidine derivative (2,6-Me(2))(4-Bpin)C(5)H(2)N when combined with B(C(6)F(5))(3) yields a frustrated Lewis pair (FLP) which reacts with H(2) to give the salt [(2,6-Me(2))(4-Bpin)C(5)H(2)NH][HB(C(6)F(5))(3)] (1). Similarly 2,2 '-(C(5)H(2)(4,6-Me(2))N)(2) and (4,4 '-(C(5)H(2)(4,6-Me(2))N)(2) were also combined with B(C(6)F(5))(3) and exposed to H(2) to give [(2,2 '-HN(2,6-Me(2))C(5)H(2)C(5)H(2)(4,6-Me(2))N][HB(C(6)F(5))(3)] (2) and [(4,4 '-HN(2,6-Me(2))C(5)H(2)C(5)H(2)(2,6-Me(2))N] [HB(C(6)F(5))(3)] (3), respectively. The mono-pyridine-N-oxide 4,4 '-N(2,6-Me(2))C(5)H(2)C(5)H(2)(2,6-Me(2))NO formed the adduct (4,4 '-N(2,6-Me(2))C(5)H(2)C(5)H(2)(2,6-Me(2))NO)(B(C(6)F(5))(3)) (4) which reacts further with B(C(6)F(5))(3) and H(2) to give [(4,4 '-HN(2,6-Me(2))C(5)H(2)C(5)H(2)(2,6-Me(2)) NO)B(C(6)F(5))(3)] [HB(C(6)F(5))(3)] (5). In a related sense, 2-amino-6-CF(3)-C(5)H(3)N reacts with B(C(6)F(5))(3) to give (C(5)H(3)(6-CF(3))NH)(2-NH(B(C(6)F(5))(3))) (6). Similarly, the species, 2-amino-quinoline, 8-amino-quinoline and 2-hydroxy-6-methyl-pyridine were reacted with B(C(6)F(5))(3) to give the products as (C(9)H(6)NH)(2-NHB(C(6)F(5))(3)) (7), (C(9)H(6)N)(8-NH(2)B(C(6)F(5))(3)) (8) and (C(5)H(3)(6-Me)NH)(2-OB(C(6)F(5))(3)) (9), respectively; while 2-amino-6-picoline, 2-amino-6-CF(3)-pyridine, 2-amino-quinoline, 8-amino-quinoline and 2-hydroxy-6-methyl-pyridine react with ClB(C(6)F(5))(2) to give the species (C(5)H(3)(6-R)NH)(2-NH-(ClB(C(6)F(5))(2))) (R = Me (10), R = CF(3) (11)) (C(9)H(6)NH)(2-NH(ClB(C(6)F(5))(2))) (12), (C(9)H(6)N)(8-NH(2)ClB(C(6)F(5))(2)) (13) and (C(5)H(3)(6-Me)NH)(2-OClB(C(6)F(5))(2)) (14), respectively. In a similar manner, 2-amino-6-picoline and 2-amino-quinoline react with B(C(6)F(5))(2)H to give (C(5)H(3)(6-Me)NH)(2-NH(HB(C(6)F(5))(2))) (15) and (C(9)H(6)NH)(2-NH(HB(C(6)F(5))(2))) (16). The corresponding reaction of 8-amino-quinoline yields (C(9)H(6)N)(8-NHB(C(6)F(5))(2)) (17). In a similar fashion, reaction of 2-amino-6-CF3-pyridine resulted in the formation of (18) formulated as (C(5)H(3)(6-CF(3))N)-(2-NH(B(C(6)F(5))(2)). Finally, treatment of 15 with iPrMgCl gave (C(9)H(6)N)(2-NH(B(C(6)F(5))(2))) (19). Crystallographic studies of 1, 2, 4, 6, 7, 10, 11, 12 and 15 are reported.
Erscheinungsjahr
Zeitschriftentitel
Dalton Transactions
Band
41
Zeitschriftennummer
7
Seite
2131-2139
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Caputo CB, Geier SJ, Winkelhaus D, et al. Reactions of substituted pyridines with electrophilic boranes. Dalton Transactions. 2012;41(7):2131-2139.
Caputo, C. B., Geier, S. J., Winkelhaus, D., Mitzel, N. W., Vukotic, V. N., Loeb, S. J., & Stephan, D. W. (2012). Reactions of substituted pyridines with electrophilic boranes. Dalton Transactions, 41(7), 2131-2139. doi:10.1039/c1dt11820j
Caputo, C. B., Geier, S. J., Winkelhaus, D., Mitzel, N. W., Vukotic, V. N., Loeb, S. J., and Stephan, D. W. (2012). Reactions of substituted pyridines with electrophilic boranes. Dalton Transactions 41, 2131-2139.
Caputo, C.B., et al., 2012. Reactions of substituted pyridines with electrophilic boranes. Dalton Transactions, 41(7), p 2131-2139.
C.B. Caputo, et al., “Reactions of substituted pyridines with electrophilic boranes”, Dalton Transactions, vol. 41, 2012, pp. 2131-2139.
Caputo, C.B., Geier, S.J., Winkelhaus, D., Mitzel, N.W., Vukotic, V.N., Loeb, S.J., Stephan, D.W.: Reactions of substituted pyridines with electrophilic boranes. Dalton Transactions. 41, 2131-2139 (2012).
Caputo, Christopher B., Geier, Stephen J., Winkelhaus, Daniel, Mitzel, Norbert W., Vukotic, V. Nicolas, Loeb, Stephen J., and Stephan, Douglas W. “Reactions of substituted pyridines with electrophilic boranes”. Dalton Transactions 41.7 (2012): 2131-2139.

5 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Tris(pentafluorophenyl)borane as an efficient catalyst in the guanylation reaction of amines.
Antiñolo A, Carrillo-Hermosilla F, Fernández-Galán R, Martínez-Ferrer J, Alonso-Moreno C, Bravo I, Moreno-Blázquez S, Salgado M, Villaseñor E, Albaladejo J., Dalton Trans 45(26), 2016
PMID: 27278089
Heterolytic activation of hydrogen using frustrated Lewis pairs containing tris(2,2',2''-perfluorobiphenyl)borane.
Binding SC, Zaher H, Mark Chadwick F, O'Hare D., Dalton Trans 41(30), 2012
PMID: 22511223
Fixation of carbon dioxide and related small molecules by a bifunctional frustrated pyrazolylborane Lewis pair.
Theuergarten E, Schlösser J, Schlüns D, Freytag M, Daniliuc CG, Jones PG, Tamm M., Dalton Trans 41(30), 2012
PMID: 22588317
Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine.
Winkelhaus D, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 41(30), 2012
PMID: 22688949
Metal-free catalytic olefin hydrogenation: low-temperature H2 activation by frustrated Lewis pairs.
Greb L, Oña-Burgos P, Schirmer B, Grimme S, Stephan DW, Paradies J., Angew Chem Int Ed Engl 51(40), 2012
PMID: 22936428

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