1147458-75-0

Upstream product

• 1214264-88-6 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 536-74-3 phenylacetylene 
• 5656-71-3 2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 479-27-6 naphthalene-1,8-diamine 
• 201852-49-5 potassium (E)-trifluoro(styryl)borate 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 100-42-5 styrene 

Relevant academic research and scientific papers

Catalyst-free and eco-friendly synthesis of masked haloarylboronic acids R (alkyl or aryl)-B(dan) on water

An environment-friendly methodology for the synthesis of R (alkyl or aryl)-B(dan) on water is described. 1,8-diamino naphthalene(danH2) was reacted with different types of organoboronic acids to furnish the products in moderate to excellent yields. A multi-gram scale reaction is also performed to ensure the scalability of the reaction.

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a

Ruthenium-Catalyzed (Z)-Selective Hydroboration of Terminal Alkynes with Naphthalene-1,8-diaminatoborane

The metal-catalyzed (Z)-selective hydroboration of terminal alkynes is synthetically challenging due to the usually (E)-selective nature of the hydroboration and the formation of the thermodynamically unstable (Z)-isomer. Herein, we report that N-heterocyclic-carbene-ligated ruthenium complexes catalyze the (Z)-selective hydroboration of terminal alkynes with H-B(dan) (dan = naphthalene-1,8-diaminato), which generates a diverse range of synthetically valuable (Z)-alkenylboranes. Mechanistic studies, particularly the isolation of a catalytically relevant borylruthenium complex, revealed a mechanism that involves the insertion of the alkyne into a Ru-B bond, which provides a catalytic cycle that is distinctly different from that of previously reported (Z)-selective hydroborations. The direct cross-coupling of the obtained (Z)-alkenyl-B(dan) enables the rapid synthesis of biologically active Combretastatin A-4 analogues.

NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes

An air-stable N-heterocyclic carbene-copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan). The newly synthesized complex can be directly activated by hydroboranes without a cocatalyst such as a base, and exhibits high reactivity for the hydroboration of alkynes under mild conditions. A gram-scale hydroboration of terminal phenylacetylene demonstrated the applicability of the copper complex for the preparation of alkenyl boronates.

Asymmetric Synthesis of α-Aminoboronic Acid Derivatives by Copper-Catalyzed Enantioselective Hydroamination

A copper-catalyzed regio- and enantioselective hydroamination of alkenyl dan boronates (dan =1,8-diaminonaphthyl) with hydrosilanes and hydroxylamines proceeds to deliver the chiral α-aminoboronic acids in good yields with high enantiomeric ratios. The ke

A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates

We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.

Iron catalysis and water: A synergy for refunctionalization of boron

A new catalytic system has been optimized to promote the conversion of boron species into others. FeCl3 associated with imidazole and water favors boron refunctionalization under mild conditions. Georg Thieme Verlag Stuttgart New York.

Rhodium-catalyzed dehydroborylation of styrenes with Naphthalene-1,8- diaminatoborane [(dan)BH]: New synthesis of masked β-borylstyrenes as new phenylene-vinylene cross-coupling modules

Styrene derivatives underwent dehydroborylation with naphthalene-1,8- diaminatoborane [(dan)BH] in the presence of a cationic rhodium complex, giving β-borylstyrene derivatives in good yields. Thus prepared β-borylstyrenes bearing a chlorine or B(pin) group on their aromatic rings were utilized for the synthesis of highly conjugated molecules through stepwise cross-coupling, taking advantage of the dan group as an effective protective group for a boronyl group.

Synthesis of B-protected β-styrylboronic acids via iridium-catalyzed hydroboration of alkynes with 1,8-naphthalenediaminatoborane leading to iterative synthesis of oligo(phenylenevinylene)s

Hydroboration of aromatic and aliphatic alkynes with 1,8- naphthalenediaminatoborane ((dan)BH) proceeded in the presence of [IrCl(cod)]2 complex with a DPPM or DPEphos ligand, affording alkenylboronic acids whose boronyl groups are masked by th