Intramolecular pyridine-based frustrated Lewis-pairs

Körte LA, Warner R, Vishnevskiy Y, Neumann B, Stammler H-G, Mitzel NW (2015)
Dalton Transactions 44(21): 9992-10002.

Journal Article | Published | English

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Abstract
Deprotonation of the methylpyridines 2,6-lutidine, 2-picoline, 4-dimethylamino-2,6-dimethylpyridine as well as 2,6-dimethyl-4-(piperidine-1-yl) pyridine with n-butyllithium or n-butyllithium/KO-t-Bu at the methyl positions led to the corresponding organolithium or -potassium compounds. Treatment with ClB(C6F5)(2) resulted in formation of the 2-borylmethylpyridines py-CH2-B(C6F5)(2). They are monomeric and form intramolecular B-N bonds and four-membered rings. A short intramolecular B-N distance was observed in the crystal structure of the dimethylamino-functionalized derivative and proposed to be responsible for the low reactivity of the products towards hydrogen, thf, acetonitrile and CO2. Hydroboration of 6-tert-butyl-2-but-4'-enylpyridine with HB(C6F5)(2) led to the corresponding hydroboration product t-Bu-py-(CH2)(4)-(C6F5)(2) which shows no intramolecular B-N bond formation due to steric crowding. H/D-scrambling experiments with a H-2/D-2 mixture revealed its reactivity towards hydrogen.
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Körte LA, Warner R, Vishnevskiy Y, Neumann B, Stammler H-G, Mitzel NW. Intramolecular pyridine-based frustrated Lewis-pairs. Dalton Transactions. 2015;44(21):9992-10002.
Körte, L. A., Warner, R., Vishnevskiy, Y., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2015). Intramolecular pyridine-based frustrated Lewis-pairs. Dalton Transactions, 44(21), 9992-10002.
Körte, L. A., Warner, R., Vishnevskiy, Y., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2015). Intramolecular pyridine-based frustrated Lewis-pairs. Dalton Transactions 44, 9992-10002.
Körte, L.A., et al., 2015. Intramolecular pyridine-based frustrated Lewis-pairs. Dalton Transactions, 44(21), p 9992-10002.
L.A. Körte, et al., “Intramolecular pyridine-based frustrated Lewis-pairs”, Dalton Transactions, vol. 44, 2015, pp. 9992-10002.
Körte, L.A., Warner, R., Vishnevskiy, Y., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Intramolecular pyridine-based frustrated Lewis-pairs. Dalton Transactions. 44, 9992-10002 (2015).
Körte, Leif Arne, Warner, Robin, Vishnevskiy, Yury, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Intramolecular pyridine-based frustrated Lewis-pairs”. Dalton Transactions 44.21 (2015): 9992-10002.
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