Issue 50, 2018

Homologation chemistry with nucleophilic α-substituted organometallic reagents: chemocontrol, new concepts and (solved) challenges

Abstract

The transfer of a reactive nucleophilic CH2X unit into a preformed bond enables the introduction of a fragment featuring the exact and desired degree of functionalization through a single synthetic operation. The instability of metallated α-organometallic species often poses serious questions regarding the practicability of using this conceptually intuitive and simple approach for forming C–C or C–heteroatom bonds. A deep understanding of processes regulating the formation of these nucleophiles is a precious source of inspiration not only for successfully applying theoretically feasible transformations (i.e. determining how to employ a given reagent), but also for designing new reactions which ultimately lead to the introduction of molecular complexity via short experimental sequences.

Graphical abstract: Homologation chemistry with nucleophilic α-substituted organometallic reagents: chemocontrol, new concepts and (solved) challenges

Article information

Article type
Feature Article
Submitted
28 mar 2018
Accepted
17 may 2018
First published
17 may 2018
This article is Open Access
Creative Commons BY license

Chem. Commun., 2018,54, 6692-6704

Homologation chemistry with nucleophilic α-substituted organometallic reagents: chemocontrol, new concepts and (solved) challenges

L. Castoldi, S. Monticelli, R. Senatore, L. Ielo and V. Pace, Chem. Commun., 2018, 54, 6692 DOI: 10.1039/C8CC02499E

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