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Keywords = diboron reagents

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15 pages, 5858 KiB  
Article
Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies
by Lucilla Favero, Andrea Menichetti, Cosimo Boldrini, Lucrezia Margherita Comparini, Valeria Di Bussolo, Sebastiano Di Pietro and Mauro Pineschi
Molecules 2021, 26(23), 7399; https://doi.org/10.3390/molecules26237399 - 6 Dec 2021
Cited by 2 | Viewed by 3830
Abstract
The possibility to form new C–B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report [...] Read more.
The possibility to form new C–B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2pin2) in a regioselective nucleophilic addition reaction under copper catalysis. Full article
(This article belongs to the Special Issue Synthesis and Application of Organoboron Derivatives)
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16 pages, 7307 KiB  
Review
Unsymmetrical Diboron Reagents: Application in Borylation Reactions of Unsaturated Bonds
by Siyi Ding, Liang Xu and Zongcheng Miao
Molecules 2019, 24(7), 1325; https://doi.org/10.3390/molecules24071325 - 4 Apr 2019
Cited by 25 | Viewed by 5863
Abstract
In the past decades, borylation reactions have received extensive research interest and have developed into effective tools in the synthesis of versatile organoboron compounds. Boranes and symmetrical diboron compounds are commonly utilized as borylating reagents in these transformations, especially in the borylation reactions [...] Read more.
In the past decades, borylation reactions have received extensive research interest and have developed into effective tools in the synthesis of versatile organoboron compounds. Boranes and symmetrical diboron compounds are commonly utilized as borylating reagents in these transformations, especially in the borylation reactions of unsaturated bonds. More recently, several types of unsymmetrical diboron reagents have been synthesized and applied in these borylation reactions, allowing for complementary chemo- and regioselectivity. This review aimed to highlight the recent development in this rising research field, focusing on new reactivity and selectivity that originates from the use of these unsymmetrical diboron reagents. Full article
(This article belongs to the Special Issue Stereogenic Centers)
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12 pages, 1293 KiB  
Communication
Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process
by Siyi Ding, Qiang Ma, Min Zhu, Huaping Ren, Shaopeng Tian, Yuzhen Zhao and Zongcheng Miao
Molecules 2019, 24(3), 377; https://doi.org/10.3390/molecules24030377 - 22 Jan 2019
Cited by 9 | Viewed by 4279
Abstract
A direct metal-free transformation from arylamines to aryl naphthalene-1,8-diamino boronamides, a type of masked boronic acid, has been developed based on Sandmeyer-type reactions. A nonsymmetrical diboron reagent, B(pin)-B(dan), was utilized as the borylating reagent, and the B(dan) moiety was transferred to the aim [...] Read more.
A direct metal-free transformation from arylamines to aryl naphthalene-1,8-diamino boronamides, a type of masked boronic acid, has been developed based on Sandmeyer-type reactions. A nonsymmetrical diboron reagent, B(pin)-B(dan), was utilized as the borylating reagent, and the B(dan) moiety was transferred to the aim products selectively. This conversion tolerated a series of functional groups, including chloro, bromo, fluoro, ester, hydroxy, cyano and amide. Full article
(This article belongs to the Special Issue Recent Development on Metal-Free Catalysis)
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16 pages, 5505 KiB  
Review
Recent Synthesis Developments of Organoboron Compounds via Metal-Free Catalytic Borylation of Alkynes and Alkenes
by Yanmei Wen, Chunmei Deng, Jianying Xie and Xinhuang Kang
Molecules 2019, 24(1), 101; https://doi.org/10.3390/molecules24010101 - 28 Dec 2018
Cited by 58 | Viewed by 10838
Abstract
Diboron reagents have been traditionally regarded as “Lewis acids”, which can react with simple Lewis base to create a significant nucleophilic character in one of boryl moieties. In particular, bis(pinacolato)diboron (B2pin2) reacts with simple Lewis bases, such as N [...] Read more.
Diboron reagents have been traditionally regarded as “Lewis acids”, which can react with simple Lewis base to create a significant nucleophilic character in one of boryl moieties. In particular, bis(pinacolato)diboron (B2pin2) reacts with simple Lewis bases, such as N-heterocyclic carbenes (NHCs), phosphines and alkoxides. This review focuses on the application of trivalent nucleophilic boryl synthon in the selective preparation of organoboron compounds, mainly through metal-free catalytic diboration and the β-boration reactions of alkynes and alkenes. Full article
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)
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