Phosphine promoted substituent redistribution reactions of B-chlorocatechol borane: molecular structures of ClBcat, BrBcat and L·ClBcat (cat = 1,2-O2C6H4; L = PMe3, PEt3, PBut3, PCy3, NEt3)†

Coapes, R. Benjamin; Souza, Fabio E. S.; Fox, Mark A.; Batsanov, Andrei S.; Goeta, Andrés E.; Yufit, Dimitrii S.; Leech, Michael A.; Howard, Judith A. K.; Scott, A. J.; Clegg, William; Marder, Todd B.

doi:10.1039/b010025k

Cited by 65 publications

(43 citation statements)

References 43 publications

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“…2, Table 1), confirming that the H-B bond of 1 has added to the alkene group in an exo fashion [23]. The boron oxygen bond distances of B(1)-O(1) 1.361(2) and B(1)-O(2) 1.361(4) Å are similar to those reported previously for 1 [14] and the B(1)-C(24) bond distance of 1.599(3) Å is within the range reported for other diorganyloxyboranes [24][25][26][27][28][29]. More significantly, the C(24)-C(29) bond length of 1.559(3) Å is typical for a single bond.…”

Section: Resultssupporting

confidence: 85%

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

Hunter

Vogels

Decken

et al. 2011

Inorganica Chimica Acta

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Section: Resultssupporting

confidence: 85%

“…The short C(8)-C(9) distance of 1.3335(18) Å illustrates that the alkene has not been reduced, as compared to the C(5)-C(8) single bond length of 1.4671(17) Å. Bond distances and angles for the boron atom are typical of related organoboronate esters [28,42].…”

Section: Resultsmentioning

confidence: 92%

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

Hunter

Vogels

Decken

et al. 2011

Inorganica Chimica Acta

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“…2,3, 38 In contrast combination of stoichiometric CatBCl and AlCl 3 in arene solvents resulted in effectively no reaction at 25°C (by 11 B and 27 Al NMR spectroscopy). With similar B-Cl bond strengths expected for BCl 3 and CatBCl (B-Cl bond lengths are 1.75 and 1.74 Å , respectively), 39,40 the lack of reactivity with CatBCl is attributed to the stabilization afforded by adopting a linear geometry at boron in the resultant borinium cation.…”

Section: Resultsmentioning

confidence: 73%

Chelate Restrained Boron Cations for Intermolecular Electrophilic Arene Borylation

Grosso¹,

Pritchard²,

et al. 2009

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Highly electrophilic boron species that borylate arenes are generated by halide abstraction from CatBX (Cat = catecholato, C 6 H 4 O 2 2-, X = Cl or Br) by [Et 3 Si][CbBr 6 ] (CbBr 6 = [closo-1-H-CB 11 H 5 Br 6 ] -). A transient [CatB][CbBr 6 ] related species reacts as a synthetic equivalent of [CatB] þ in intermolecular electrophilic borylation, with reactions proceeding rapidly at 25°C. The [CatB] þ moiety was shown to be strongly Lewis acidic on the basis of 1 H and 31 P{ 1 H} NMR spectroscopy of the crotonaldehyde and triethylphosphine oxide adducts, respectively. Catalytic quantities of [Et 3 Si][CbBr 6 ] and CatBX were effective for the high-yielding borylation of arenes by CatBH in a highly atom efficient cycle with H 2 the only byproduct. Successful catalysis was dependent on the robust [CbBr 6 ] -anion and the use of electrophile-resistant borane sources.

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“…Attempts to crystallize compound 3 in MeOH resulted in a single crystal X-ray diffraction study on 3', ( Figure 2, Table 1) where the pinacol group has been cleaved, and replaced with one hydroxyl group and one methoxy group on the boron atom. The B-O bond distances of 1.3532(19) and 1.363(2) Å are typical for those observed in other three coordinate boron compounds [41][42][43][44]. No appreciable intermolecular interaction between the Lewis acidic boron atom and the amide groups is observed in the solid state.…”

Section: Resultsmentioning

confidence: 55%