The transition metal catalyzed hydroboration of enamines

Geier, Michael J.; Vogels, Christopher M.; Decken, Andreas; Westcott, Stephen A.

doi:10.1016/j.jorganchem.2009.05.016

Cited by 19 publications

(12 citation statements)

References 56 publications

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“…One possible explanation that accounts for distribution of deuterium to both carbons is a tandem two-step dehydrogenative borylation and reduction. 14 …”

Section: Resultsmentioning

confidence: 99%

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Surprisingly facile C–H activation in the course of oxime-directed catalytic asymmetric hydroboration

Thacker

Shoba

Geis

et al. 2015

Tetrahedron Letters

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“…One possible explanation that accounts for distribution of deuterium to both carbons is a tandem two-step dehydrogenative borylation and reduction. 14 …”

Section: Resultsmentioning

confidence: 99%

“…While the formation of a mixture of deuterated isomers 11a and 11b is an additional puzzling aspect, a well-documented dehydrogenative borylation mechanism may be involved to account for the deuterium scrambling. 14 …”

Section: Resultsmentioning

confidence: 99%

Surprisingly facile C–H activation in the course of oxime-directed catalytic asymmetric hydroboration

Thacker

Shoba

Geis

et al. 2015

Tetrahedron Letters

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“…To gain further insight into the nature of products formed during these reactions, we therefore investigated reactions of vinylarenes using HBdd and [Cp*IrCl 2 ] 2 as a catalyst precursor. Considerable recent interest has focussed on the hydroboration [32][33][34][35][36][37][38] and subsequent transformation [39] of these important substrates. While reactions of 4-vinylanisole (4-MeOC 6 H 4 CH@CH 2 ) with HBcat and HBpin using a catalytic amount of [Cp*IrCl 2 ] 2 proceed to give the terminal hydScheme 1.…”

Section: Resultsmentioning

confidence: 99%

[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine

Hunter

Vogels

Decken

et al. 2011

Inorganica Chimica Acta

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“…This compound in fact appears in a number of manifestations as it seems to readily form co-crystals (Lee & Wallwork, 1978;Hosomi et al, 2000;Matsuoka et al, 1988;Zhu et al, 2014). No examples were found of oxadiazole rings at the end of the alkane chains; indeed, the only derivatives with simple fivemembered rings in that position were dioxaborolane derivatives (Kalinin et al, 2003;Geier et al, 2009). In contrast, 1,3,4oxadiazole-2-thiones are far less abundant with only 29 unique organic structures reported.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure of 5-[2-(9H-carbazol-9-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione

Mohamed¹,

El‐Emary²,

Albayati³

2017

Acta Cryst E

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The title compound, C 16 H 13 N 3 OS, comprises an oxadiazolethione ring bound to the N atom of an almost planar carbazole ring system (r.m.s. deviation = 0.0088 Å ) through an ethylene chain. The oxadiazole ring is inclined to the the carbazole ring system by 40.71 (6) . In the crystal, N-HÁ Á ÁO, N-HÁ Á ÁS, C-HÁ Á ÁN and C-HÁ Á ÁS hydrogen bonds combine with C-HÁ Á Á (ring) andcontacts to stack the molecules along the b-axis direction. Chemical contextCarbazole derivatives have been shown to have several industrial applications including use in optoelectronic devices (Fitilis et al., 2007;Peng et al., 2011), dye-sensitized solar cells (Li et al., 2010) and photochromic dyes (Billah et al., 2008). Moreover, fused heterocycles with carbazole scaffolds are noted for their biological activities. They are found in drugs such as tubingensin A and B and have been shown to have both antiviral and cytotoxic activities (TePaske et al., 1989). The anti-inflammatory agents caprofen and etodolaca and the antipyretic agent nincazole (Ghoneim et al., 2006) are also carbazole based. The biological activity of so many carbazolebased heterocycles encouraged us to synthesize the title compound and its molecular crystal structure is reported here. Structural commentaryIn the title compound C 16 H 13 N 3 OS, (I), the oxadiazolethione ring binds to the carbazole ring system through a C2-C3-C4-N3 ethylene chain with the ring systems inclined at an angle of ISSN 2056-9890 40.71 (6) , Fig. 1. The carbazole ring system is almost planar with the outer C5-C10 and C11-C16 benzene rings subtending angles of 0.38 (13) and 0.64 (13) , respectively, to the central N3/C5/C10/C11/C16 ring. Bond lengths and angles in both ring systems are normal and similar to those found in the numerous other carbazole structures (see, for example, Kimura et al., 1985) and those of the few known oxadiazolethione derivatives with alkane chains at C5 (Khan et al. 2014;Zheng et al. 2006). Supramolecular featuresIn the crystal, classical N1-H1NÁ Á ÁO1 and N1-H1NÁ Á ÁS1 hydrogen bonds form C(4) chains of molecules linked in a head-to-head fashion along the b-axis direction, Fig. 2. These contacts are bolstered by the C4 atom acting as a bifurcated donor forming weaker C4-H4AÁ Á ÁN2 hydrogen bonds and C4-H4BÁ Á ÁCg4 interactions, Table 1. In the chains, the mean plane of the oxadiazole ring is inclined at 10.7 to (101). The N-HÁ Á ÁO and N-HÁ Á ÁS hydrogen bonds also impose close O1Á Á ÁN2(x, y À 1, z) contacts of 2.9516 (18) Å . Adjacent chains are further linked by C3-H3BÁ Á ÁS1 hydrogen bonds that form inversion dimers, enclosing R 2 2 (12) rings. This combination of contacts stacks molecules along the b-axis direction, Fig. 3. Adjacent oxadiazole rings form dimers through Cg1Á Á ÁCg1 vi -contacts with centroid-to-centroid separations of 3.3931 (9) Å Cg1 is the centroid of the O1/C2/ N3/N4/C5 ring; symmetry code: (vi) 1 À x, 1 À y, 1 À z]. These dimers are linked by much weaker C12-H12Á Á ÁCg4 interactions, Table 1 The molecular structure of (I) with ellipsoi...

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The transition metal catalyzed hydroboration of enamines

Cited by 19 publications

References 56 publications

Surprisingly facile C–H activation in the course of oxime-directed catalytic asymmetric hydroboration

Surprisingly facile C–H activation in the course of oxime-directed catalytic asymmetric hydroboration

[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine

Crystal structure of 5-[2-(9H-carbazol-9-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione

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