Homolytic cleavage of diboron(4) compounds using diazabutadiene derivatives

Verma, Piyush Kumar; Meher, Naresh Kumar; Geetharani, K.

doi:10.1039/d1cc02881b

Cited by 5 publications

(2 citation statements)

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“…In this system, the addition of a catalytic amount of 4-cyanopyridine was effective, and the authors suggested that the catalyst might act as a single-electron acceptor in the homolytic cleavage of boron–boron bonds. They also demonstrated the application of this system to the catalytic reduction of azo-compounds via the radical diboration of azoarenes, and the corresponding products were obtained in good to excellent yields ( Scheme 18 ) [ 99 , 100 , 101 ].…”

Section: Boron-centered Interelement Compounds In Radical Addition Re...mentioning

confidence: 99%

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Yamamoto

2023

Molecules

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In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward the establishment of a resource-recycling society. In organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and the recycling of elemental resources in mind, rather than just only synthesis. Many studies on the construction of frameworks of functional molecules using ionic reactions and transition-metal-catalyzed reactions have been reported, but most of them have focused on the formation of carbon–carbon bonds. However, it is essential to introduce appropriate functional groups at appropriate positions in molecules in order for the molecules to express their functions, and furthermore, the highly selective preparation of multiple functional groups is considered important for the creation of new functional molecules. In this review, we focus on radical reactions with high functional group selectivity and overview the recent progress in practical methods for the simultaneous introduction of multiple functional groups and propose future synthetic strategies that emphasize the recycling of elemental resources and environmental friendliness.

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Section: Boron-centered Interelement Compounds In Radical Addition Re...mentioning

confidence: 99%

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Yamamoto

2023

Molecules

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“…Because of the hybridization of the valence s 2 p 1 to sp 2 electron deficiency configuration, boron can form diverse cluster motifs that are functional building blocks in materials science, medicine, organometallic/coordination chemistry, and more. − Over the past few decades, joint experimental techniques combined with theoretical investigations have revealed the interesting structures and properties of boron clusters, especially the metal-doped boron clusters. − Clusters formed by three B atoms have been shown to possess unique bonding and aromaticity in recent reports. , Diboron reagents have been traditionally regarded as “Lewis acids”, which are utilized as reagents in borylation reactions and other reactions with simple Lewis base. , Pubill-Ulldemolins et al have investigated that the B–B moiety can destroy CC bond to form new B–C bond with low energy barrier in the reactions of alkene with [MeO-pinB-Bpin] ‑ …”

Section: Introductionmentioning

confidence: 99%

Boron-Mediated C–C and C≡N Bond Cleavage of Acetonitrile: Matrix Infrared Spectra and Theoretical Calculations

et al. 2023

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The reactions of laser-ablated B atoms with acetonitrile in 4 K solid neon have been investigated by matrixisolation infrared spectra, and new products have been identified by 10 B, D, and 13 C isotopic substitutions and quantum chemical calculations. The side-on complex B-η 2 -(NC)-CH 3 was observed during deposition and isomerized to NCBCH 3 , CNBCH 3 , and CNB(H)�CH 2 , respectively, through C−C bond breakage and hydrogen transfer. For diboron reaction with acetonitrile, the Nend-on complex BBNCCH 3 was formed on deposition, which rearranged to HBNC(B)�CH 2 and HBNBC�CH 2 by λ > 220 nm irradiation. In this reaction pathway, the C�N triple bond was completely cleaved. The final diboron product HBNBC�CH 2 was much more stable than the precursors by 152.0 kcal mol −1 at the CCSD(T)-Full/cc-pVTZ//B3LYP/aug-cc-pVTZ level of theory.

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Catalyst‐Free Diborylation and Silaboration of Azoarenes: A Simple Photoinduced Approach

Mondal,

Pal,

Geetharani

2024

Angewandte Chemie

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The diborylation of the N=N double bond of azoarenes has been achieved using a commercially available diboron reagent, B2cat2 [bis(catecholato)diboron]. By utilizing the photo‐switchable nature of azoarenes under blue‐LED light irradiation, an uncatalyzed diborylation and silaboration yielded a broad range of functionalized hydrazine derivatives. The mechanistic origin validates the importance of cis configuration, which is corroborated by theoretical calculations.

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Homolytic cleavage of diboron(4) compounds using diazabutadiene derivatives

Abstract: Diazabutadiene derivatives have been identified as a distinct class of reagents, capable of cleaving B-B bond of the diboron(4). The cleavage is accompanied by formation of a new C=C bond...

Cited by 5 publications

References 50 publications

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Boron-Mediated C–C and C≡N Bond Cleavage of Acetonitrile: Matrix Infrared Spectra and Theoretical Calculations

Catalyst‐Free Diborylation and Silaboration of Azoarenes: A Simple Photoinduced Approach

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