Successive Iodine−Magnesium or −Copper Exchange Reactions for the Selective Functionalization of Polyhalogenated Aromatics

Yang, Xuan; Rotter, Thomas; Piazza, Claudia; Knöchel, Paul

doi:10.1021/ol0341492

Cited by 53 publications

(12 citation statements)

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“…Functionalized organozinc, organoindium, and organocopper reagents. [36][37][38][39][40][41][42] Scheme 7. Palladium-catalyzed cross-coupling of organoindium reagents with electrophiles bearing acidic protons.…”

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confidence: 99%

Regio‐ and Chemoselective Metalation of Arenes and Heteroarenes Using Hindered Metal Amide Bases

et al. 2011

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The preparation of highly functionalized organometallic compounds can be achieved by direct C-H activation of a broad range of unsaturated substrates using lithium chloride solubilized 2,2,6,6-tetramethylpiperidide bases (TMP(n)MX(m)⋅p LiCl). These are excellent reagents for converting a wide range of aromatic and heterocyclic substrates into valuable organometallic reagents with broad applications in organic synthesis.

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Regio‐ and Chemoselective Metalation of Arenes and Heteroarenes Using Hindered Metal Amide Bases

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“…However, in the para and meta cases such a directing effect is absent, and as a consequence it is more difficult to accomplish the halogen-lithium exchange reaction without decomposition of the resulting organolithium species. However, such problems can be solved by choosing aryl iodides as precursors [35] in flow microreactor systems ( Figure 15). [36] Organometallic compounds that bear a cyano group are also very important because the activating effect of the cyano group, such as the ortho-directing effect, and its transformation into various other functional groups are advantageous from a synthetic point of view.…”

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confidence: 99%

Green and Sustainable Chemical Synthesis Using Flow Microreactors

2010

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Several features that allow flow microreactors contribute to green and sustainable chemical synthesis are presented: (1) For extremely fast reactions, kinetics often cannot be used because of the lack of homogeneity of the reaction environment when they are conducted in batch macroreactors. Better controllability, by virtue of fast mixing based on short diffusion paths in microreactors, however, leads to a higher selectivity of the products, based on kinetics considerations. Therefore, less waste is produced. (2) Reactions involving highly unstable intermediates usually require very low temperatures when they are conducted in macrobatch reactors. By virtue of short residence times, flow microreactors enable performing such reactions at ambient temperatures, avoiding cryogenic conditions and minimizing the energy required for cooling. (3) By virtue of the precise residence time control, flow microreactors allow to avoid the use of auxiliary substances such as protecting groups, enabling highly atom- and step-economical straightforward syntheses. The development of several test plants based on microreaction technology has proved that flow microreactor synthesis can be applied to the green and sustainable production of chemical substances on industrial scales. (4) Microreactor technology enables on-demand and on-site synthesis, which leads to less energy for transportation and easy recycling of substances.

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“…Bemerkenswerterweise sind solche Metallreagentien mit den meisten funktionellen Gruppen kompatibel, die in der organischen Synthese anzutreffen sind, wie in den funktionalisierten Organometallverbindungen 19-24 abgebildet (Schema 6). [36][37][38][39][40][41][42][43][44] Demzufolge ermçglicht das chirale Organozinkreagens 19, nach Jackson et al synthetisiert, die rasche Synthese zahlreicher chiraler a-Aminosäuren. [37] Eine Umsetzung bei tiefen Temperaturen, gefolgt von einer Transmetallierung mit ZnBr 2 , liefert das bei Raumtemperatur stabile Vinyl-Carbenoid 20, wie von Snieckus gezeigt wurde.…”

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Regio‐ und chemoselektive Metallierung von Arenen und Heteroarenen mit gehinderten Metallamidbasen

et al. 2011

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Die Synthese hoch funktionalisierter Organometallverbindungen gelingt durch C‐H‐Aktivierung zahlreicher ungesättigter Substrate mit Lithiumchlorid‐solubilisierten 2,2,6,6‐Tetramethylpiperidyl‐Basen (TMPnMXm⋅p LiCl). Diese Reagentien erweisen sich als exzellent zur Umwandlung vielfältiger aromatischer sowie heterocyclischer Substrate in nützliche metallorganische Reagentien mit weiter Anwendungsbreite in der organischen Synthese.

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Successive Iodine−Magnesium or −Copper Exchange Reactions for the Selective Functionalization of Polyhalogenated Aromatics

Cited by 53 publications

References 20 publications

Regio‐ and Chemoselective Metalation of Arenes and Heteroarenes Using Hindered Metal Amide Bases

Regio‐ and Chemoselective Metalation of Arenes and Heteroarenes Using Hindered Metal Amide Bases

Green and Sustainable Chemical Synthesis Using Flow Microreactors

Regio‐ und chemoselektive Metallierung von Arenen und Heteroarenen mit gehinderten Metallamidbasen

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