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An Efficient and Reliable Catalyst System Using Hemilabile Aphos for B ‐Alkyl Suzuki–Miyaura Cross‐Coupling Reaction with Alkenyl Halides (Eur. J. Org. Chem. 5/2013)
Author(s) -
Ye Ning,
Dai WeiMin
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201390009
Subject(s) - chemistry , denticity , halide , catalysis , alkyl , chelation , palladium , medicinal chemistry , catalytic cycle , organic chemistry , metal
The cover picture shows a snapshot of the blooming canola field in Southwest China. The catalytic cycle illustrates the P,O‐chelating and P‐monodentate complexation modes of the hemilabile Aphos‐Y with palladium(0) and the reductive elimination of the P,O‐chelating palladium(II) species derived from an alkyl borinate and an alkenyl halide under mild conditions (K 3 PO 4 · 3H 2 O, THF/H 2 O, r.t.). It is considered that switching between the P,O‐chelating and P‐monodentate complexation modes facilitates various steps in the whole catalytic cycle. The usefulness of the Aphos‐Y–Pd(OAc) 2 catalyst in the “9‐MeO‐9‐BBN variant” of the Suzuki–Miyaura cross‐coupling reaction used for the total synthesis of complex natural products has been demonstrated. Details are discussed in the Short Communication by N. Ye and W.‐M. Dai on p. 831 ff.