77855-70-0Relevant academic research and scientific papers
A STEREOSPECIFIC SYNTHESIS OF CONJUGATED (E,Z)- AND (Z,Z)-ALKADIENES BY A PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH 1-ALKENYL BROMIDES
Miyaura, Norio,Suginome, Hiroshi,Suzuki, Akira
, p. 127 - 130 (1981)
The reactions of (Z)-1-alkenyldisiamylboranes with (Z)- or (E)-1-alkenyl bromides in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium and sodium ethoxide gave the corresponding conjugated (Z,Z)- or (Z,E)-alkadiene with high ster
Novel and Convenient Method for the Stereo- and Regiospecific Synthesis of Conjugated Alkadienes and Alkenynes via the Palladium-Catalyzed Cross-Coupling Reaction of 1-Alkenylboranes with Bromoalkenes and Bromoalkynes
Miyaura, Norio,Yamada, Kinji,Suginome, Hiroshi,Suzuki, Akira
, p. 972 - 980 (2007/10/02)
Details of a new and general method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes are described.The reaction of (E)- or (Z)-1-alkenyldisiamylboranes, or 2-((E)-1-alkenyl)-1,3,2-benzodioxaboroles readily obtainable by hydroboration, with either (E)- or (Z)-1-alkenyl bromides in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium and bases such as sodium alkoxides gives the corresponding (E,E)-, (E,Z)-, (Z,E)-,or (Z,Z)-conjugated alkadienes stereo- and regiospecifically, while retaining the configurations of both the strating alkenylboranes and bromoalkenes.The reaction of (E)- and (Z)-1-alkenyldisiamylboranes with 1-bromoalkynes similarly provides a stereo- and regiospecific synthesis of conjugated (E)- and (Z)-alkenynes.A mechanism of this cross-coupling reaction, which involves the transmetalation between a 1-alkenylborane and an alkoxypalladium(II) complex generated through the metathetical displacement of a halogen atom from R(Pd(II)X with sodium alkoxide, is proposed.
