0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
1.4.3 Alkenylzinc Cross-Coupling Reactions

DOI: 10.1055/sos-SD-207-00519

Mejuch, T.; Marek, I.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20131765.

General Introduction

Carbon—carbon bond-forming reactions are arguably one of the most important synthetic transformations in chemistry as they represent essential steps in the building of more complex molecules from simple precursors. For many years, organic chemists have been developing a plethora of reactions for carbon—carbon bond formation between molecules with saturated sp3 carbon atoms. However, until the discovery and development of metal-mediated cross-coupling reactions, beginning in the 1970s, there were no simple, general, and direct methods available for carbon—carbon bond formation between unsaturated species such as vinyl, aryl, and alkynyl moieties. In the subsequent decades this paradigm for carbon—carbon bond construction has allowed chemists to assemble complex molecular frameworks encompassing total synthesis of natural products, medicinal chemistry, and industrial process development, as well as chemical biology, materials, and nanotechnology. The emergence of cross coupling as a popular method in synthesis arises from both the diversity of organometallic reagents utilized in these reactions and the broad range of functional groups that can be incorporated into these reagents.

Me eeee eeeeeee, eee eeee eeeee eeee ee ee eee eeeeeeeee eeeee-eeeeeeee eeeeeeeee ee eeeeeeeeeee eeeeeeee. Meeeeee eee ee-eeeeeee eeee eeeeeeeeeee eeeeeee ee eee eeeeeeeeeee ee eeee eeeee-eeeeeeee eeeeeeee eee, eeeeeeeee, eeee eeee ee eeeeeeee ee eeeeee eee Meeeeee eeeee-eeeeeeee eeeeeeee. Me eeee eeeee eeeeeeeeeee eeeeeeeeeee eeee eeeeee ee ee eeeeeeee ee eeeee eeeeeee eeeeeeeeeee eeee ee eeeeeeeee, eeeeee, eeeeeeeee, eeeeeee, eee eeeee. Meee eeeeeeeeeee eee eeeee ee eeeeeee eeeeeeeee eeee eeeeeee.

Me eeeeeeee ee eeeeeeeeeeeee eeeeeeee, eeeeeee ee eeeee eeeee eeeeeeeeee, eeeeeeeeee eeeeeee eeeeeee e eeeee eeeeeeeeee eeeee eeeeeeeee.[‌8‌] Meee eeee eeeeeeee eeeeeee eeeeeee ee eeeeeeeee eeeeeeee eee eeee eeee e eeeeeee. Me eeeeee eeeee eeee ee eee eeee eee eeeeeee eeee eeeeeeeeee eeeeeeeee eee eeeeeee ee eeeeeeeeee e eeee eeeee ee eeeeeeeeeeeeeee eeeeeeeee ee e eeeeee ee eee eeeeeeee ee eeeee eee-eeeee e-eeeeeeee eeee eee eeeeeee eeeeeeee eeee eee e-eeeeeeee ee eeee eeeeeeeeee eeeeee, eeeeeee ee eeee eeeeeeee eeeeeeeeeeeee.[‌8‌,‌8‌] Mee eeeee eeeeee eee eeeeeeeeee eeee eeeeeeee eee eeee ee eeeeeee eeeeeeee eeeeeeeeeeeeee eeeeeeeeeeeee, eeeee eee eeeeeee ee eeeeeeee eeee eeee eeeeeeeeeeeee eeee eee eeeeeeeeee eeeeee eeeeeeeeeee. Meee eee ee eeeeeeeee ee eee eeeeeeee ee e-eeeeeeee ee eee eeeeeeeeee-eeeee eeeeee, eeeee eeeee e eeeeee ee eee eeeeeeee eeeeeeee eeeeeeeee eeee eeee eee eeeeeeeeee ee eee eeee eeeeeeeeee eeeee eee eeeee e-eeeeeeee ee eeee eee eee eeee ee eeeeee ee eeeeeeeeeee ee eeee eeeeeee eeeeeeeee. Mee eeeeeeeeeee ee eee eeee eeeeeeeee ee eeeeeeeeee eeeeeeeeeee eeeeee eeeeeeeeee eeeeee eee eeee eeeeeeeeeeeeeee ee eeee eeeeeeeeee-eeeee eeeeeeeee eeeee eeeeeeeeeee eeeeeeee eeeeeeee. Meeeeeeeee eeeeeeeee eee eee eeeeeeeeeeeeeeee ee eeeeeeeeee eeeeee eeeeeeee eeee eeeeeeeee eeeeeeeeeeeee,[‌8‌‌8‌] eeeee eeeee eeeee-eeeeeeee eeeeeeeee eeee eeee eeeeeeeeee (Meeeee 8).

Meeeee 8 Meeeeee Meeeeeeee Meeee eee eee Meeeeee Meeee-Meeeeeee Meeeeeee

Meeee eeeeeeeee eeeeeee ee eeeeeeeeee eeeeeeee eee ee eeeee: (e) eeeeeeeeee eeeeeee ee eeeeeee eeeeeee M8MeM, (e) eeeeeeeeeeeee ee eeeeeee eeeeeee M8MeM8 ee eeeee M8 eee M8 eee eee eeeeeee eeeeee, eee (e) eeeeeeeeeeeeee ee eeeeeee eeeeeee (M8)(M8)(M8)MeM [ee eeeee eee eeeee (M) ee eeeeeee Me ee MeM].[‌8‌] Mee eeeeeeeeee ee eeeee eeee eeeeeeee eeeeeeeee eeee eee eeeeee ee eeeeee eeeeeeee eeeeee ee eee eeee eeeeee (e.e., M8MeM < M88Me < M88MeMeM < M88MeMe). Mee eeeeeeeeee ee eeeeeeeeee eeeeeee eeeeeeee eeeeeee ee eee eeeeeeeeeeeeeeeee ee eee eeeeee eeeeeeee ee eeee eee ee eee eeeeeeeeeee ee eee eeee eeeeeee. M eeeeeeeeeeeee ee eee eeeeeeee eeeeeeeeeee eeeeee ee eeeeeeeee ee eeeeeeeee eeeeeee eeeee ee e eeee eeeee eeeeee—eeee eeee eee ee e eeeeee eeeeeeeeee (eeeeeee < eeeee < eeeeeee ≤ eeee < eeeeee < eeeee).