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Insertion Reactions of 1,2-Disubstituted Olefins with an α-Diimine Palladium(II) Complex by Carla Carfagna; Giuseppe Gatti; Luca Mosca; Paola Paoli; Annalisa Guerri is a Chemistry article available to read on EtoBox.

What is Insertion Reactions of 1,2-Disubstituted Olefins with an α-Diimine Palladium(II) Complex about?

## Abstract The migratory insertions of __cis__ or __trans__ olefins CH(X)CH(Me) (X = Ph, Br, or Et) into the metal–acyl bond of the complex [Pd(Me)(CO)(^i^Pr~2~dab)]^+^ [B{3,5‐(CF~3~)~2~C~6~H~3~}~4~]^−^ (1) (^i^Pr~2~dab = 1,4‐diisopropyl‐1,4‐diazabuta‐1,3‐diene = __N,N′__‐(ethane‐1,2‐diylidene)bis[1‐methylethanamine]) are described (__Scheme 1__). The resulting five‐membered palladacycles were characterized by NMR spectroscopy and X‐ray analysis. Experimental data reveal some important aspects concerning the regio‐ and stereochemistry of the insertion process. In particular, the presence of a Ph or Br substituent at the alkene leads to the formation of highly regiospecific products. Moreover, in all cases, the geometry of the substituents in the formed palladacycle was the same as in the starting olefin, as a consequence of a __cis__ addition of the Pd–acyl fragment to the CC bond. Reaction with CO and MeOH of the five‐membered complex derived from __trans‐β__‐methylstyrene (= [(1__E__)‐prop‐1‐enyl]benzene) insertion, yielded the 2,3‐substituted __γ__‐keto ester 9 with an (2__RS__,3__SR__)‐configuration (__Scheme 3__).

Who reads Insertion Reactions of 1,2-Disubstituted Olefins with an α-Diimine Palladium(II) Complex?

Author

Carla Carfagna; Giuseppe Gatti; Luca Mosca; Paola Paoli; Annalisa Guerri

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

2006

Language

EN

Field

Chemistry (Physical Sciences)