Catecholborane

Lane, Clinton F.; Kabalka, George W.

doi:10.1016/s0040-4020(01)83219-1

Cited by 116 publications

(51 citation statements)

References 49 publications

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“…Similar reactivity was observed with chelating bidentate systems Ir(acac)-(P-P) 2 to give the corresponding species Ir(dppm)(η 6 -catBcat) (dppm = 1,1-diphenylphosphanomethane, 4), Ir(dppe)(η 6 -catBcat) (dppe = 1,2-diphenylphosphanoethane, 5) and Ir(dppp)(η 6 -catBcat) (dppp = 1,3-diphenylphosphanopropane, 6, Scheme 2). It should be noted that the precursor Ir(acac)(dppe) had to be prepared using microwave radiation [13] as conventional heating of Ir(acac)-(coe) 2 In this study, complexes 3-6 have been characterized by a number of physical methods including multinuclear NMR spectroscopy. The 11 B NMR spectroscopic data for these species is consistently between δ = 14.8-15.2 ppm, which is only slightly different from the monophosphane PCy 3 species at δ = 13.9 ppm.…”

Section: Resultssupporting

confidence: 72%

“…[1] Although borane reagents H 3 B · X (X = THF, SMe 2 ) add readily to alkenes at -80°C, [2] other hydroboration reagents, such as diorganyloxyboranes, are slow to react even at room temperature. For instance, catecholborane (HBcat, cat = 1,2-O 2 C 6 H 4 ) and pinacolborane (HBpin, pin = 1,2-O 2 C 2 Me 4 ) add to alkenes and alkynes only at elevated temperatures [3] or in the presence of a transition metal catalyst.…”

Section: Introductionmentioning

confidence: 99%

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Iridium Phosphane Complexes Containing Arylspiroboronate Esters for the Hydroboration of Alkenes

et al. 2011

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Iridium phosphane arylspiroboronate esters have been prepared by addition of B 2 cat 3 (cat = 1,2-O 2 C 6 H 4 ) to the iridium precursors Ir(acac)(coe) 2 /PR 3 (acac = acetylacetonato, coe = cis-cyclooctene) or Ir(acac)(coe) 2 /P-P (chelating bidentate ligands) at elevated temperatures. These novel complexes have been characterized by a number of physical methods including X-ray diffraction studies for the PCy 3 (2) and dppp (6, 1,3-diphenylphosphanopropane) derivatives. The arylspiroboronate esters, as seen with the more common rhodium

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Section: Resultssupporting

confidence: 72%

Section: Introductionmentioning

confidence: 99%

Iridium Phosphane Complexes Containing Arylspiroboronate Esters for the Hydroboration of Alkenes

et al. 2011

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“…To avoid problems associated with the in situ formation of the boronate, pure boronates 3 a-c were prepared and distilled under inert atmosphere prior to use. [19] The reaction of pure 3 a with tetranitromethane (1 equiv) gave 2 a in 60-75 % yield (GC). Due to product contamination by traces of 9 a, the dinitrooxime ether 2 a must be chromatographed twice, which results in a decreased isolated yield (58 %).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Unusual Oxime Ethers by Reaction of Tetranitromethane with B‐Alkylcatecholboranes

Lüthy

Schenk

Renaud

2010

Chemistry A European J

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The reaction of tetranitromethane with B-alkylcatecholboranes leads to the formation of unusual dinitrooxime ethers. A tentative mechanism is provided, which suggests the involvement of extremely fast addition of alkyl radicals to tetranitromethane. The substitution of one of the nitro groups in the oxime ethers by nucleophiles (such as secondary amines, halogens and styrene) and by radicals generated from B-alkylcatecholboranes is reported.

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“…Thus, the treatment of borane-THF and catechol readily provides catecholborane, a very mild reducing and hydroborating agent (eq 90) (151). The reducing characteristics of catecholborane have been explored in detail (152). This reagent has been a favorite for transition metal catalyzed hydroborations (153) …”

Section: ••Hq-imentioning

confidence: 99%

Sixty Years of Hydride Reductions

Brown

Ramachandran

1996

ACS Symposium Series

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We are nearing the close of a century that witnessed unprecedented scientific and technological progress that was probably unimaginable even half a century ago. While the overall advancement of science and technology is phenomenal, in reality it has taken place over several generations, made possible by the untiring dedication of the scientists involved to their research. In fact, every decade achieved significant advances, permitting the next generation to move forward in their own pursuit of knowledge. Later developments might cause some of the work of the earlier workers to appear trivial. However, one can only admire the tenacity of the pioneers whose steadfastness has led us to where we are today.In chemistry, the invention and perfection of new sophisticated instruments and methodologies have facilitated the analysis of reaction intermediates and products. Newer industries catering to the needs of chemists have decreased the necessity of having to prepare many of the starting materials and reagents.

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Catecholborane

Cited by 116 publications

References 49 publications

Iridium Phosphane Complexes Containing Arylspiroboronate Esters for the Hydroboration of Alkenes

Iridium Phosphane Complexes Containing Arylspiroboronate Esters for the Hydroboration of Alkenes

Synthesis of Unusual Oxime Ethers by Reaction of Tetranitromethane with B‐Alkylcatecholboranes

Sixty Years of Hydride Reductions

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