Catecholborane

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title: "Catecholborane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["benzene-derivatives", "organoboron-compounds", "boranes"] topic_path: "general/benzene-derivatives" source: "https://en.wikipedia.org/wiki/Catecholborane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|Watchedfields = changed |verifiedrevid = 427312003 |Name = Catecholborane |ImageFile = Catecholborane structure.png |ImageFile1 = Catecholborane-3D-spacefill.png |ImageAlt1 = Catecholborane molecule |PIN = 2H-1,3,2-Benzodioxaborole |OtherNames = 7,9-dioxa-8λ2-borabicyclo[4.3.0]nona-1,3,5-triene |Section1={{Chembox Identifiers |SMILES = [B]1OC2=CC=CC=C2O1 |ChemSpiderID_Ref = |ChemSpiderID = 10617125 |InChI = 1/C6H5BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4,7H |InChIKey = CENMEJUYOOMFFZ-UHFFFAOYAI |SMILES1 = c1cccc2OBOc12 |StdInChI_Ref = |StdInChI = 1S/C6H5BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4,7H |StdInChIKey_Ref = |StdInChIKey = CENMEJUYOOMFFZ-UHFFFAOYSA-N |CASNo_Ref = |CASNo = 274-07-7 |UNII_Ref = |UNII = UB69382H5J |PubChem = 6327445 |EC_number = 205-991-5 |Section2={{Chembox Properties |Formula = C6H5BO2 |MolarMass = 119.92 g/mol |Appearance = Colorless liquid |Density = 1.125 g/cm3, liquid |MeltingPtC = 12 |BoilingPtC = 50 |BoilingPt_notes = at 50 mmHg |Section7={{Chembox Hazards |NFPA-H = 1 | NFPA-F = 4 | NFPA-R = 2 | NFPA-S = W |GHSPictograms = |GHSSignalWord = Danger |HPhrases = |PPhrases = |FlashPtC = 2

Catecholborane (abbreviated HBcat) is an organoboron compound that is useful in organic synthesis. This colourless liquid is a derivative of catechol and a borane, having the formula C6H4O2BH.

Synthesis and structure

Traditionally catecholborane is produced by treating catechol with borane (BH3) in a cooled solution of THF. However, this method results in a loss of 2 mole equivalents of the hydride. Nöth and Männig described the reaction of alkali-metal boron hydride (LiBH4, NaBH4, KBH4) with tris(catecholato)bisborane in an ethereal solvent such as diethyl ether. In 2001, Herbert Brown and coworkers prepared catecholborane by treatment of tri-o-phenylene bis-borate with diborane.

Unlike borane itself or alkylboranes, catechol borane exists as a monomer. This behavior is a consequence of the electronic influence of the aryloxy groups that diminish the Lewis acidity of the boron centre. Pinacolborane adopts a similar structure.

Reactions

Catecholborane is less reactive in hydroborations than borane-THF or borane-dimethylsulfide.

When catecholborane is treated with a terminal alkyne, a trans vinylborane is formed: :C6H4O2BH + HC2R → C6H4O2B-CHCHR The product is a precursor to the Suzuki reaction and is the only borane which stops at the alkene instead of reacting further to the alkane.

Catecholborane may be used as a stereoselective reducing agent when converting β-hydroxy ketones to syn 1,3-diols.

Catecholborane oxidatively adds to low valent metal complexes, affording boryl complexes. :C6H4O2BH + Pt(PR3)2 → (C6H4O2B)Pt(PR3)2H

References

References

  1. [http://www.freepatentsonline.com/4739096.html Process for producing catecholborane – Patent 4739096]
  2. (2000). "New Economical, Convenient Procedures for the Synthesis of Catecholborane". Organic Process Research & Development.
  3. Janice Gorzynski Smith, ''Organic Chemistry: Second Ed''. 2008. pp 1007
  4. (1990). "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-octadiene".
  5. (2016). "Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse". Chemical Reviews.

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benzene-derivativesorganoboron-compoundsboranes