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.

Homologation chemistry with nucleophilic α-substituted organometallic reagents: Chemocontrol, new concepts and (solved) challenges / L. Castoldi, S. Monticelli, R. Senatore, L. Ielo, V. Pace. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - 54:50(2018 Jun 25), pp. 6692-6704. [10.1039/c8cc02499e]

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

L. Castoldi
Primo
;
2018-06-25

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.
Settore CHIM/06 - Chimica Organica
17-mag-2018
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/890737
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