(E)-(2-Bromoethenyl)diisopropoxyborane. A New Building Block for (E)-Olefins

Abstract

(E)-(2-Bromoethenyl)diisopropoxyborane is a useful precursor for the synthesis of (E)-olefins by the stepwise cross-coupling reaction with organozinc chlorides and then with organic halides in the presence of a base, both catalyzed by Pd complex.

Haloboration: scope, mechanism and utility

“…[69][70][71] During their fundamental studies, Lappert et al used esterification of R-BX 2 with catechol or alkanols to transform their products into stable and conveniently analysed derivatives. 12,37 Esterification by ether cleavage 72 or by reaction with the respective alcohol 73 gave boronic esters with prolonged shelf-life. 25 Other functionalisation includes formation of R-B(dan) (dan = 1,8-diaminonaphthalen-N,N 0diyl), 74 R-B(MIDA) complexes (MIDA = N-Methyliminodiacetate), 75 or R-BF 3 K salts.…”

Suzuki Polycondensation: Polyarylenes à la Carte

“…Its AB-type trans congener 14 was reported even earlier and obtained by the addition of BBr 3 to acetylene. [80] A g-borylallylboron compound 15, which was prepared by metathesizing pinacol allyl-and vinylboronate, might also be an interesting candidate for SPC.…”

Rubredoxin reductase from Alcanivorax borkumensis: Expression and characterization

“…Finally and perhaps more as a curiosity it should be mentioned that compound 10 had already been used in the early 1990s to convert mono‐ and disubstituted acetylenes into compound 13 , a potential SPC monomer,79 by a Pt‐catalyzed route. Its AB‐type trans congener 14 was reported even earlier and obtained by the addition of BBr 3 to acetylene 80. A γ ‐borylallylboron compound 15 , which was prepared by metathesizing pinacol allyl‐ and vinylboronate, might also be an interesting candidate for SPC 50…”