815581-73-8

Upstream product

• 870530-90-8 [C₆H₄C(O)N(CH(CH₃)2)2]B(OCH(CH₃)2)2 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 20383-28-2 N,N-diisopropyl benzamide 
• 103681-98-7 2-diisopropylaminocarbonylphenylboronic acid 
• 73183-34-3 bis(pinacol)diborane 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 7154-66-7 2-bromobenzoic acid chloride 
• 88-65-3 2-bromobenzoic-acid 
• 79839-66-0 o-bromo-N,N-diisopropylbenzamide 

Downstream Products

• 815581-74-9 [C₆H₄CH₂NH(CH(CH₃)2)2]BF₃ 
• 95753-26-7 2-[(N,N-diisopropylamino)methyl]phenylboronic acid 

Relevant academic research and scientific papers

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Amide Effects in C?H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides

A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O???K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C?H activation/borylation.

Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts: 2-N,N-Diisopropylaminophenylboronate derivatives

Directed ortho-metallation is used to introduce a boron function into N,N-diisopropylbenzamide, resulting in the formation of both borinate and boronate derivatives. N,N-Diisopropylbenzamide ortho-boronate pinacol ester can be reduced with sodium borohydr

BIFUNCTIONAL CATALYSTS

Bifunctional Lewis acid - Lewis base catalyst of Formula (I): wherein O is a C2-60 optionally heteroatom containing substituted or unsubstituted hydrocarbon scaffold comprising pendant or integral bifunctional groups LA and LB wherein LA is a pendant or integral boron or silicon Lewis acid group and LB is a pendant or integral phosphorus or nitrogen Lewis base group and its salts, N-fanctionalised derivatives, dimer or oligomer thereof; processes for the preparation thereof; novel compounds and novel intermediates; a composition comprising a catalyst or compound of the invention; a kit comprising one or more catalysts; the use thereof as catalysts in selective transformations, kits therefor and processes for selective transformation reactions catalysed thereby; screening methods to identify catalysts for specific transformations; and kits therefor.