Functionalized Organometallic Reagents

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Availability

Availability

Preparation via Insertion Grignard s Synthesis Generally Considered as a Radical Process

Schlenk Equilibrium Parasite Reactions Reversible Reaction in THF Substitution Reactions

Preparation via Permutation Towards the Most Stable Magnesium Species Relative Stabilities Relative Stabilities

TurboGrignard Reagent Preparation via Permutation Isopropylmagnesium chloride lithium chloride

Form C sp 3 to C sp 2 Preparation via Permutation - Increased functional group compatibility - Mild reaction conditions, including a convenient range of temperatures - Side reactions inhibited - Allows for preparation of functionalized heteroaryl organometallics - Large-scale production of Grignard reagents possible

Form C sp 3 to C sp 2 Preparation via Permutation

Form C sp 3 to C sp 2 Preparation via Permutation

Form C sp 3 to C sp 2 Preparation via Permutation

Form C sp 3 to C sp 2 Preparation via Permutation

Form C sp 3 to C sp 2 - Heteroaromatic Preparation via Permutation

Form C sp 3 to C sp 2 Alkenyl-Mg Preparation via Permutation

Form C sp 3 to C sp 2 Preparation via Permutation

In the Presence of an Acidic Proton Preparation via Permutation

In the Presence of an Acidic Proton Preparation via Permutation

In the Presence of an Acidic Proton Preparation via Permutation

In the Presence of an Acidic Proton Preparation via Permutation

In the Presence of an Acidic Proton Preparation via Permutation

Permutation of Sulfoxides

Permutation of Sulfoxides

Permutation of Sulfoxides

Permutation of Sulfoxides

Permutation of Sulfoxides

Exception of 2-Pyridinyl Sulfoxides

Exception of 2-Pyridinyl Sulfoxides Pentavalent Sulfur Species S. Oae et al. Tetrahedron Lett. 1984, 25, 69.

Exception of 2-Pyridinyl Sulfoxides

Case of Halogeno-cyclopropanes Configurationally Stable

Case of Halogeno-cyclopropanes

Preparation via Transmetallation Mechanism Will Not Be Discussed in Details «s-bond Metathesis» or «Substitution Mechanism»

Preparation via Transmetallation

Notation To Simplify Preparation via Transmetallation Grignard are easily prepare Transmetallation is not so commun to generate organomagnesium

From Lithium Enolates to Magnesium Enolates Preparation via Transmetallation Deprotonation with Grignard Reagents Uneasy Transmetallation Quite Easy Due to a Relatively Better Stability of Organomagnesium Species

From Lithium Enolates to Magnesium Enolates Preparation via Transmetallation

From Lithium Enolates to Magnesium Enolates Preparation via Transmetallation

From Lithium Enolates to Magnesium Enolates Preparation via Transmetallation

From Lithium Enolates to Magnesium Enolates Preparation via Transmetallation

From Lithium Enolates to Magnesium Enolates Preparation via Transmetallation

Preparation via Transmetallation 1,4-Additions towards Magnesium Enolates SPECIFIC EXAMPLES

Preparation via Transmetallation 1,4-Additions towards Magnesium Enolates SPECIFIC EXAMPLES

Preparation via Transmetallation 1,4-Additions towards Magnesium Enolates SPECIFIC EXAMPLES Aza-Michael Addition

Preparation via Transmetallation 1,4-Additions towards Magnesium Enolates SPECIFIC EXAMPLES Thio-Michael Addition

Reactivity of Organomagnesium Preparation via Transmetallation

Reactivity of Magnesium Enolates Preparation via Transmetallation

Other Reactivities Preparation via Transmetallation

Organozinc Reagents Preparation via Insertion - Smooth Reactivity Towards Electrophiles - Easily Prepared by Transmetallation - Can Be Used at Room Temperature - High Functional Group Tolerance

Organozinc Reagents Preparation via Insertion

Organozinc Reagents Preparation via Insertion

Organozinc Reagents Activation of Zn Preparation via Insertion Zn (0) + TMS-Cl (2-5 mol%) Zn (0) + dibromoethane (2-5 mol%) ZnCl2 + Li = Zn* (Rieke Zn) Zn (0) + LiCl (1 eq.)

Organozinc Reagents Activation of Zn Preparation via Insertion

Organozinc Reagents Activation of Zn Allylic Systems Preparation via Insertion

Organozinc Reagents Preparation via Insertion

Organozinc Reagents Preparation via Insertion

Organozinc Reagents Preparation via Insertion Insertion in Phosphates, Tosylates and Mesylates

Organozinc Reagents Preparation via Insertion Insertion in Phosphates, Tosylates and Mesylates

Organozinc Reagents High Functional Group Tolerance Preparation via Insertion

Organozinc Reagents From Lithium and Magnesium Preparation via Transmetallation

Organozinc Reagents From Lithium and Magnesium Preparation via Transmetallation

Organozinc Reagents From Boranes Preparation via Transmetallation

Organozinc Reagents From Boranes Preparation via Transmetallation

Organozinc Reagents From Boranes Preparation via Transmetallation

Organozinc Reagents From Boranes Preparation via Transmetallation

Organozinc Reagents From Boranes Preparation via Transmetallation

Organozinc Reagents From Boranes Preparation via Transmetallation

Organozinc Reagents From Zirconium Preparation via Transmetallation

Organozinc Reagents Alkyl and Aryl Zinc Species Reactivity of Zinc Species

Organozinc Reagents Allylzinc Species Reactivity of Zinc Species

Organozinc Reagents Allylzinc Species Reactivity of Zinc Species Stereocontrolled by Zimmermann-Traxler

Organozinc Reagents Zinc Carbenoids Reactivity of Zinc Species Guy Emschwiller, 1929 (Zn insertion) «Zinc Iodide Exchange»

Organozinc Reagents Zinc Carbenoids More Reactive Species Reactivity of Zinc Species Shi Carbenoid Charette Carbenoid

Organozinc Reagents Zinc Carbenoid Reactivity of Zinc Species

Organozinc Reagents Zinc Carbenoid in Homologations Reactivity of Zinc Species

Organozinc Reagents Zinc Carbenoid in Homologations Reactivity of Zinc Species I. Marek et al. J. Am. Chem. Soc. 2010, 132, 5588 I. Marek et al. Org. Lett. 2011, 13, 3604

Organozinc Reagents Zinc Carbenoid in Homologations Reactivity of Zinc Species I. Marek et al. Nature Chem. 2009, 1, 128 I. Marek et al. Chem. Commun. 2006, 1683

Organoalane Derivatives Preparation via Transmetallation - Special Reactivity - Highly Sensitive

Organomanganese Reagents Preparation via Transmetallation - Special Reactivity