A bromomethanetriboronic ester

Matteson, Donald S.; Davis, Roger J.; Hagelee, Leon A.

doi:10.1016/s0022-328x(00)92984-x

Cited by 36 publications

(12 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Originally, the proof of concept was established by the addition of methyllithium to tris(ethylenedioxyboryl)methane, to generate in situ the corresponding bis(ethylenedioxyboryl)methide salt, that interacts with aldehydes or ketones to give the corresponding alkene monoboronic esters (Scheme 15) [17,18]. The analogue 1,1,1-tris(boryl)methide salt has exclusively been prepared via base-assisted deborylation of the corresponding tetra(boryl)methane (C(BO 2 C 2 Me 4 ) 4 ) [19], promoting the condensation with aldehydes and ketones to obtain 1,1-gem-diborylalkenes (Scheme 16) [20]. The reactivity developed from 1,1,1-tris(boryl)alkanes offers a significant number of applications, since their activation in the presence of bases generates the corresponding carbanions, which are strongly stabilized by delocalization, with vacant p-orbitals of the remaining two boron atoms.…”

Section: Synthetic Applicationsmentioning

confidence: 99%

Tri(boryl)alkanes and Tri(boryl)alkenes: The Versatile Reagents

Salvadó

Fernández

2020

Molecules

View full text Add to dashboard Cite

The interest of organoboron chemistry in organic synthesis is growing, together with the development of new and versatile polyborated reagents. Here, the preparation of 1,1,1-tri(boryl)alkanes, 1,2,3-tri(boryl)alkanes, 1,1,2-tri(boryl)alkanes, as well as 1,1,2-tri(boryl)alkenes as suitable and accessible polyborated systems is demonstrated as being easily applied in the construction of new carbon-carbon and carbon-heteroatom bonds. Synthetic procedures and limitations have been collected to demonstrate the powerful strategies to construct selective molecules, taking advantages of the easy transformation of carbon-boron bond in multiple functionalities, under the total control of chemo- and stereoselectivity.

show abstract

Section: Synthetic Applicationsmentioning

confidence: 99%

Tri(boryl)alkanes and Tri(boryl)alkenes: The Versatile Reagents

Salvadó

Fernández

2020

Molecules

View full text Add to dashboard Cite

show abstract

“…We also determined the molecular structures of 4 and 5 by single‐crystal X‐ray diffraction (see the Supporting Information) . Compounds 4 and 6 have been previously prepared in several steps by borylation of CCl 4 or CHCl 3 , and compound 7 by treating B 2 pin 2 with diazomethane in the presence of [Pt(PPh 3 ) 4 ] . Compound 5 is a novel product, although a platinum‐catalyzed double diboration of the alkyne C 2 (Bcat) 2 with B 2 cat 2 has been reported to afford the Bcat analogue of 5 , C 2 (Bcat) 6 …”

Section: Figurementioning

confidence: 99%

Fully Borylated Methane and Ethane by Ruthenium‐Mediated Cleavage and Coupling of CO

et al. 2016

View full text Add to dashboard Cite

Many transition-metal complexes and some metalfree compounds are able to bind carbon monoxide,amolecule which has the strongest chemical bond in nature.H owever, very few of them have been shown to induce the cleavage of its C À Obond and even fewer are those that are able to transform CO into organic reagents with potential in organic synthesis. This work shows that bis(pinacolato)diboron, B 2 pin 2 ,r eacts with ruthenium carbonyl to give metallic complexes containing borylmethylidyne (CBpin) and diborylethyne (pinBCCBpin) ligands and also metal-free perborylated C 1 and C 2 products, such as C(Bpin) 4 and C 2 (Bpin) 6 ,respectively,which have great potential as building blocks for Suzuki-Miyaura cross-coupling and other reactions.The use of 13 CO-enriched ruthenium carbonyl has demonstrated that the boron-bound carbon atoms of all of these reaction products arise from CO ligands.The strongest chemical bond in nature is that of carbon monoxide,which has adissociation energy of 1076 kJ mol À1 at 298 K. Therobustness of this triple bond has akey influence on the chemistry of this simple molecule.Although carbon monoxide is inexpensive and readily available,t he synthetic chemical industry only uses it as af eedstock in very few processes,s uch as the water-gas shift reaction (synthesis of CO 2 and H 2 from CO and water), the hydroformylation of olefins,t he preparation of phosgene, methanol, and acetic acid, and the Fischer-Tropsch synthesis of hydrocarbons (hydrogenation of CO).[1] Among these industrial processes,t he latter is the only one in which the CÀOb ond of carbon monoxide is cleaved. From the point of view of fundamental research, the cleavage of CO under mild reaction conditions has long been an attractive challenge because it could provide new ways of transforming CO into highly functionalized C 1 ,C 2 ,a nd C n molecules.T od ate,a part from some ruthenium and osmium carbonyl clusters,which are able to transform two CO ligands into CO 2 and acarbide ligand, [2,3] only ahandful of transitionmetal complexes are known to cleave CO ligands with [4][5][6] or without [7][8][9][10][11][12][13][14][15][16] the help of other reagents.T hese reactions have, in some cases,a fforded metal-free CO-derived organic products, [4-6, 13, 16] but all these products are hydrocarbons. In contrast, it has recently been shown that some reagents of low-valent p-block elements are able to activate free or metal-coordinated CO.Regarding boron-containing reagents, Stephan and co-workers and Erker and co-workers have reported that some frustrated Lewis pairs promote the reduction of CO with either hydrogen [17] or HB(C 6 F 5 ) 2 , [18,19] Siebert and co-workers have reported the insertion of CO into ac yclic diborane, [20] and Braunschweig and co-workers have reported the coupling of CO at ab oron-boron triple bond [21] and at ametal-boron double bond.[22] By using other p-block elements,wenote that CO can be reduced by certain singlet carbenes [23] and transient triplet carbenes, [24] ag ermylene compound can coupl...

show abstract

“…11 ) Tetrakis(dimethoxyboryl)methane, prepared from carbon tetrachloride by treatment with lithium and dimethoxyboryl chloride (Scheme 5 ), 12 ) undergoes transesterification with pinacol or 1,3-propanediol to give the corresponding tetraborylmethanes, respectively. 13 )…”

Section: Preparation Of Gem - and Vic mentioning

confidence: 99%

Polyborylated reagents for modern organic synthesis

Shimizu

Hiyama

2008

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

View full text Add to dashboard Cite

Diverse kinds of gem- and vic-diborylated compounds are now readily available thanks to advances in gem-diborylation of lithium carbenoids as well as vic-diborylation of carbon–carbon multiple bonds with diboron compounds. These diborylated reagents lead to invention of polyborylated reagents and many novel and useful synthetic methods for supreme stereocontrol. This review summarizes preparative methods and synthetic reactions of di- and polyborylated reagents with the emphasis on multiple bond formation.

show abstract

A bromomethanetriboronic ester

Cited by 36 publications

References 7 publications

Tri(boryl)alkanes and Tri(boryl)alkenes: The Versatile Reagents

Tri(boryl)alkanes and Tri(boryl)alkenes: The Versatile Reagents

Fully Borylated Methane and Ethane by Ruthenium‐Mediated Cleavage and Coupling of CO

Polyborylated reagents for modern organic synthesis

Contact Info

Product

Resources

About