Preparation of Polyfunctional Diorgano-Magnesium and -Zinc Reagents Using In Situ Trapping Halogen-Lithium Exchange of Highly Functionalized (Hetero)aryl Halides in Continuous Flow.

Title Preparation of Polyfunctional Diorgano-Magnesium and -Zinc Reagents Using In Situ Trapping Halogen-Lithium Exchange of Highly Functionalized (Hetero)aryl Halides in Continuous Flow.
Authors M. Ketels; M.Andreas Ganiek; N. Weidmann; P. Knochel
Journal Angew Chem Int Ed Engl
DOI 10.1002/anie.201706609
Abstract

We report a halogen-lithium exchange performed in the presence of various metal salts (ZnCl2, MgCl2·LiCl) on a broad range of sensitive bromo- or iodo-(hetero)arenes using BuLi or PhLi as exchange reagent and a commercially available continuous flow setup. The resulting diarylmagnesium or diarylzinc species were trapped with various electrophiles resulting in the formation of polyfunctional (hetero)arenes in high yields. This methodology enabled the functionalization of (hetero)arenes containing highly sensitive groups such as an isothiocyanate, nitro, azide or ester. A straightforward scale-up was possible without further optimization.

Citation M. Ketels; M.Andreas Ganiek; N. Weidmann; P. Knochel.Preparation of Polyfunctional Diorgano-Magnesium and -Zinc Reagents Using In Situ Trapping Halogen-Lithium Exchange of Highly Functionalized (Hetero)aryl Halides in Continuous Flow.. Angew Chem Int Ed Engl. 2017. doi:10.1002/anie.201706609

Related Elements

Magnesium

Magnesium Bohr ModelSee more Magnesium products. Magnesium (atomic symbol: Mg, atomic number: 12) is a Block S, Group 2, Period 3 element with an atomic mass of 24.3050. The number of electrons in each of Magnesium's shells is [2, 8, 2] and its electron configuration is [Ne] 3s2. The magnesium atom has a radius of 160 pm and a Van der Waals radius of 173 pm. Magnesium was discovered by Joseph Black in 1775 and first isolated by Sir Humphrey Davy in 1808. Magnesium is the eighth most abundant element in the earth's crust and the fourth most common element in the earth as a whole. Elemental MagnesiumIn its elemental form, magnesium has a shiny grey metallic appearance and is an extremely reactive. It is can be found in minerals such as brucite, carnallite, dolomite, magnesite, olivine and talc. Commercially, magnesium is primarily used in the creation of strong and lightweight aluminum-magnesium alloys, which have numerous advantages in industrial applications. The name "Magnesium" originates from a Greek district in Thessaly called Magnesia.

Zinc

See more Zinc products. Zinc (atomic symbol: Zn, atomic number: 30) is a Block D, Group 12, Period 4 element with an atomic weight of 65.38. The number of electrons in each of zinc's shells is 2, 8, 18, 2, and its electron configuration is [Ar] 3d10 4s2. Zinc Bohr ModelThe zinc atom has a radius of 134 pm and a Van der Waals radius of 210 pm. Zinc was discovered by Indian metallurgists prior to 1000 BC and first recognized as a unique element by Rasaratna Samuccaya in 800. Zinc was first isolated by Andreas Marggraf in 1746. In its elemental form, zinc has a silver-gray appearance. It is brittle at ordinary temperatures but malleable at 100 °C to 150 °C.Elemental Zinc It is a fair conductor of electricity, and burns in air at high red producing white clouds of the oxide. Zinc is mined from sulfidic ore deposits. It is the 24th most abundant element in the earth's crust and the fourth most common metal in use (after iron, aluminum, and copper). The name zinc originates from the German word "zin," meaning tin.

Lithium

Lithium Bohr ModelSee more Lithium products. Lithium (atomic symbol: Li, atomic number: 3) is a Block S, Group 1, Period 2 element with an atomic weight of 6.94. The number of electrons in each of Lithium's shells is [2, 1] and its electron configuration is [He] 2s1. The lithium atom has a radius of 152 pm and a Van der Waals radius of 181 pm. Lithium was discovered by Johann Arvedson in 1817 and first isolated by William Thomas Brande in 1821. The origin of the name Lithium comes from the Greek wordlithose which means "stone." Lithium is a member of the alkali group of metals. It has the highest specific heat and electrochemical potential of any element on the period table and the lowest density of any elements that are solid at room temperature. Elemental LithiumCompared to other metals, it has one of the lowest boiling points. In its elemental form, lithium is soft enough to cut with a knife its silvery white appearance quickly darkens when exposed to air. Because of its high reactivity, elemental lithium does not occur in nature. Lithium is the key component of lithium-ion battery technology, which is becoming increasingly more prevalent in electronics.