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      Transition-metal-free synthesis of vicinal triborated compounds and selective functionalisation of the internal C–B bond

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          Abstract

          1,2,3-Triborated compounds can be prepared by simple nucleophilic borylation of 1,3-dienes, without the assistance of metal catalysts.

          Abstract

          1,2,3-Triborated compounds can be prepared by simple nucleophilic borylation of 1,3-dienes, without the assistance of metal catalysts. Selective functionalisation of the internal C–B bond of the 1,2,3-triborated compounds, through cross-coupling with aryl iodides, highlights the powerful methodology toward polyfunctionalisation.

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          Regioselectivity of the borylation of alkanes and arenes.

          John Hartwig (2011)
          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.

            Ibraheem A I Mkhalid, Stephen Westcott, Todd Marder … (2016)
            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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              Asymmetric synthesis from terminal alkenes by diboration/cross-coupling cascades

              Scott N. Mlynarski, Christopher H. Schuster, James P. Morken (2013)
              Amongst prospective starting materials for organic synthesis, terminal (monosubstituted) alkenes are ideal. In the form of α-olefins, they are manufactured on enormous scale and they are the core product features from many organic chemical reactions. While their latent reactivity can easily enable hydrocarbon chain extension, alkenes also have the attractive feature of being stable in the presence of many acids, bases, oxidants and reductants. In spite of these impressive attributes, relatively few catalytic enantioselective transformations have been developed that transform aliphatic α-olefins in >90% ee and, with the exception of site-controlled isotactic polymerization of α-olefins, 1 none of these processes result in chain-extending C-C bond formation to the terminal carbon. 2, 3, 4, 5, 6 Herein, we describe a strategy that directly addresses this gap in synthetic methodology and present a single-flask catalytic enantioselective conversion of terminal alkenes into a range of chiral products. These reactions are enabled by an unusual neighboring group participation effect that accelerates Pd-catalyzed cross-coupling of 1,2-bis(boronates) relative to nonfunctionalized alkyl boronate analogs. In tandem with enantioselective diboration, this reactivity feature connects abundant alkene starting materials to a diverse array of chiral products. Importantly with respect to synthesis utility, the tandem diboration/cross-coupling reaction (DCC reaction) generally provides products in high yield and high selectivity (>95:5 enantiomer ratio), employs low loadings (1–2 mol %) of commercially available catalysts and reagents, it offers an expansive substrate scope, and can address a broad range of alcohol and amine synthesis targets, many of which cannot be easily addressed with current technology.
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                Author and article information

                Journal
                Journal ID (publisher-id): CHCOFS
                Title: Chemical Communications
                Abbreviated Title: Chem. Commun.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1359-7345
                ISSN (Electronic): 1364-548X
                Publication date Created: 2018
                Publication date (Electronic): 2018
                Volume: 54
                Issue: 72
                Pages: 10104-10107
                Affiliations
                [1 ]Department Química Física i Inorgànica
                [2 ]University Rovira i Virgili
                [3 ]Tarragona
                [4 ]Spain
                [5 ]Department Chemistry
                Article
                DOI: 10.1039/C8CC06153J
                SO-VID: f81e23b7-7da3-4711-ada1-4013a464e560
                Copyright © © 2018
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                http://rsc.li/journals-terms-of-use

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