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      Transition-metal-free B–B and B–interelement reactions with organic molecules

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          Abstract

          This review is a guided tour along the activation modes and reactivity of B–B, B–Si, B–N, B–S, B–Se and B–P reagents, in the absence of any transition metal complex.

          Abstract

          This review is a guided tour along the activation modes and reactivity of B–B, B–Si, B–N, B–S, B–Se and B–P reagents, in the absence of any transition metal complex. Here are disclosed the general concepts related to the homolytic and heterolytic cleavage of B–B and B–interelement bonds, as well as the generation of new C–B and C–interelement bonds, in a selective way. The greener consequences of these novel routes facilitate the gram scale preparations of target functionalised organic compounds. Intrinsic data about the suggested mechanisms and spectroscopic evidence that supports the innovative theories are provided along the review. Since this is a stimulating area of work that has emerged within the last decade, this overview serves as the basis to understand the new trends and hopefully to generate inspiration for future discoveries in the field.

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          Most cited references127

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          Regioselectivity of the borylation of alkanes and arenes.

          The borylation of alkanes and arenes has become some of the most practical C-H bond functionalization chemistry. Most striking is the high regioselectivity of these reactions. Rhodium and ruthenium complexes catalyze with exquisite selectivity the borylation of methyl C-H bonds over methylene or methine C-H bonds. Iridium complexes catalyze, with high steric control, the borylation of one aromatic C-H bond over another. In contrast, iridium-catalyzed borylation of heteroaromatic C-H bonds is more controlled by electronic effects. Detailed information on these selectivities and mechanistic information on the origins of this regioselectivity will be described in this critical review (95 references).
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            Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse.

            Although known for over 90 years, only in the past two decades has the chemistry of diboron(4) compounds been extensively explored. Many interesting structural features and reaction patterns have emerged, and more importantly, these compounds now feature prominently in both metal-catalyzed and metal-free methodologies for the formation of B-C bonds and other processes.
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              Transition Metal−Boryl Compounds:  Synthesis, Reactivity, and Structure

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                Author and article information

                Journal
                CSRVBR
                Chemical Society Reviews
                Chem. Soc. Rev.
                Royal Society of Chemistry (RSC)
                0306-0012
                1460-4744
                2017
                2017
                : 46
                : 2
                : 415-430
                Affiliations
                [1 ]Dept Física Química e Inorgánica
                [2 ]University Rovira i Virgili
                [3 ]43007 Tarragona
                [4 ]Spain
                [5 ]Dept. Química Orgánica
                [6 ]Division of Chemical Process Engineering
                [7 ]Graduate School of Engineering Hokkaido University
                [8 ]Sapporo
                [9 ]Japan
                Article
                10.1039/C6CS00692B
                27942683
                f103d476-0a11-45f7-a3bc-4766937b14db
                © 2017
                History

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