Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.
Chem Rec. 2004; 3(5):271-80.CR

Abstract

Metal-catalyzed borylation of alkenes, alkynes, arenes, and organic halides with B-B or H-B compounds has been developed for the synthesis of organoboron compounds from simple organic substrates. The platinum(0)-catalyzed addition of bis(pinacolato)diboron to alkenes and alkynes provided a method for the stereoselective synthesis of cis-bis(boryl)alkanes or cis-bis(boryl)alkenes. The addition of diboron to 1,3-dienes with platinum(0) complexes provided a new access to cis-1,4-bis(boryl)-2-butene derivatives, which are versatile reagents for diastereoselective allylboration of carbonyl compounds. The first one-step procedure for the syntheses of aryl-, vinyl-, and allylboronates was achieved via crosscoupling reactions of diborons with aryl and 1-alkenyl halides or triflates and allyl acetates. Direct C-H borylation of arenes catalyzed by a transition metal complex was studied as an economical protocol for the synthesis of a variety of arylboron derivatives. Ir-catalyzed C-H borylation of arenes, heteroarenes, and benzylic positions of alkylarenes by bis(pinacolato)diboron or pinacolborane furnished aryl-, heteroaryl-, and benzylboron compounds. This article discusses the mechanisms of these reactions and their synthetic applications.

Authors+Show Affiliations

Ishiyama T

Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan. ishiyama@org-mc.eng.hokudai.ac.jp

Miyaura N

No affiliation info available

MeSH

AlkenesAlkynesBoronBoron CompoundsCatalysisHydrocarbons, HalogenatedMetals, Heavy

Pub Type(s)

Journal Article

Language

eng

PubMed ID

14762827

Citation

Ishiyama, Tatsuo, and Norio Miyaura. "Metal-catalyzed Reactions of Diborons for Synthesis of Organoboron Compounds." Chemical Record (New York, N.Y.), vol. 3, no. 5, 2004, pp. 271-80.

Ishiyama T, Miyaura N. Metal-catalyzed reactions of diborons for synthesis of organoboron compounds. Chem Rec. 2004;3(5):271-80.

Ishiyama, T., & Miyaura, N. (2004). Metal-catalyzed reactions of diborons for synthesis of organoboron compounds. Chemical Record (New York, N.Y.), 3(5), 271-80.

Ishiyama T, Miyaura N. Metal-catalyzed Reactions of Diborons for Synthesis of Organoboron Compounds. Chem Rec. 2004;3(5):271-80. PubMed PMID: 14762827.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Metal-catalyzed reactions of diborons for synthesis of organoboron compounds. AU - Ishiyama,Tatsuo, AU - Miyaura,Norio, PY - 2004/2/6/pubmed PY - 2004/3/19/medline PY - 2004/2/6/entrez SP - 271 EP - 80 JF - Chemical record (New York, N.Y.) JO - Chem Rec VL - 3 IS - 5 N2 - Metal-catalyzed borylation of alkenes, alkynes, arenes, and organic halides with B-B or H-B compounds has been developed for the synthesis of organoboron compounds from simple organic substrates. The platinum(0)-catalyzed addition of bis(pinacolato)diboron to alkenes and alkynes provided a method for the stereoselective synthesis of cis-bis(boryl)alkanes or cis-bis(boryl)alkenes. The addition of diboron to 1,3-dienes with platinum(0) complexes provided a new access to cis-1,4-bis(boryl)-2-butene derivatives, which are versatile reagents for diastereoselective allylboration of carbonyl compounds. The first one-step procedure for the syntheses of aryl-, vinyl-, and allylboronates was achieved via crosscoupling reactions of diborons with aryl and 1-alkenyl halides or triflates and allyl acetates. Direct C-H borylation of arenes catalyzed by a transition metal complex was studied as an economical protocol for the synthesis of a variety of arylboron derivatives. Ir-catalyzed C-H borylation of arenes, heteroarenes, and benzylic positions of alkylarenes by bis(pinacolato)diboron or pinacolborane furnished aryl-, heteroaryl-, and benzylboron compounds. This article discusses the mechanisms of these reactions and their synthetic applications. SN - 1527-8999 UR - https://www.unboundmedicine.com/medline/citation/14762827/Metal_catalyzed_reactions_of_diborons_for_synthesis_of_organoboron_compounds_ DB - PRIME DP - Unbound Medicine ER -

Tags

Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.Chem Rec. 2004; 3(5):271-80.CR