Premium
An Efficient and Reliable Catalyst System Using Hemilabile Aphos for B ‐Alkyl Suzuki–Miyaura Cross‐Coupling Reaction with Alkenyl Halides
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.201201602
Subject(s) - chemistry , catalysis , ligand (biochemistry) , alkyl , medicinal chemistry , halide , coupling reaction , nonane , substrate (aquarium) , solvent , stereochemistry , combinatorial chemistry , organic chemistry , receptor , biochemistry , oceanography , geology
Abstract The 9‐methoxy‐9‐borabicyclo[3.3.1]nonane‐based B ‐alkyl Suzuki–Miyaura cross‐coupling reaction (the 9‐MeO‐9‐BBN variant) has been efficiently performed by using the catalyst consisting of Pd(OAc) 2 and a hemilabile P,O‐ligand, Aphos‐Y, under mild reaction conditions (K 3 PO 4 · 3H 2 O, THF/H 2 O, room. temp.). For applications in the total synthesis of structurally complex natural products, the Johnson protocol commonly uses two ligands (dppf and Ph 3 As) and two organic solvents (THF and DMF). In contrast, the new version reported here employs one ligand (Aphos‐Y) and one organic solvent (THF). Moreover, the broad substrate scope and the excellent functional group tolerance of the Pd(OAc) 2 –Aphos‐Y catalyst have been demonstrated, providing a reliable and simple synthetic tool for fragment coupling in total synthesis through formation of a C(sp 3 )–C(sp 2 ) bond.