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Reactivity of C,N-chelated organoboron compounds with lithium anilides - formation of unexpected 1,2,3-trisubstituted 1H-2,1-benzazaboroles
Authors: Hejda Martin | Lyčka Antonín | Jambor Roman | Růžička Aleš | Dostál Libor
Year: 2013
Type of publication: článek v odborném periodiku
Name of source: Dalton Transactions
Publisher name: Royal Society of Chemistry
Place: Cambridge
Page from-to: 6417-6428
Titles:
Language Name Abstract Keywords
cze Reaktivita C,N-chelatovaných organoboritých sloučenin s organolitnými amidy C,N-koordinované borány obsahující ligandy L1-3 (L-1 = [o-(CH=NtBu)C6H4], L-2 = [o-(CH=N-2,6-iPr(2)C(6)H(3))C6H4], L-3 = [o-(CH2NMe2)C6H4]) byly charakterizovány pomoci NMR spektroskopie. Reaktivita; C,N-cheláty; organoborité sloučeniny; NMR
eng Reactivity of C,N-chelated organoboron compounds with lithium anilides - formation of unexpected 1,2,3-trisubstituted 1H-2,1-benzazaboroles A set of C, N-intramolecularly coordinated boranes containing various C, N-chelating ligands L1-3 (where L-1 = [o-(CH=NtBu)C6H4], L-2 = [o-(CH=N-2,6-iPr(2)C(6)H(3))C6H4], L-3 = [o-(CH2NMe2)C6H4]); L1-3BCl2 (for 1 L = L-1, for 2 L = L-2, for 5 L = L-3), (LBPhCl)-B-1 (3) and (LBCy2)-B-1 (4) (where Cy = cyclohexyl) were synthesized and fully characterized by multinuclear NMR spectroscopy and in cases of 1 and 3-5 by the single crystal X-ray diffraction analysis. The reaction of 1-3 with the anilides ArNHLi (Ar = 2,6-Me2C6H3 or 2,6-iPr(2)C(6)H(3)) proceeded via unexpected addition of anilide across the CvN bond yielding 1,2,3-trisubstituted 1H-2,1-benzazaboroles 6-11, whose structures were unambiguously established by single crystal X-ray diffraction analysis (except for 11) and multinuclear NMR spectroscopy. In contrast, compounds 4 and 5 were inert towards ArNHLi. The investigation dealing with the reaction mechanism between the parent boranes 1-3 and ArNHLi revealed that amidolithiation of the CvN double bond involved in the ligand backbones is the crucial step of the whole reaction. The CvN double bond in 1-3 is activated by its coordination to the ortho bonded Lewis acidic boron center, which was also proven by the fact that the non-substituted ligand L1H did not react with ArNHLi under the same reaction conditions in an analogous reaction. bond covalent radii; x-ray structures; coordination chemistry; bis(alkylamido)phenylborane complexes; 1;2-azaborolyl complexes; tetrahedral character; arylboronic acids; amine complexes; lewis-acid; boron

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