Stereo-defined synthesis of differentially all-carbon tetrasubstituted alkenes derived from ( E )-1-bromo-2-iodoalkenes

Regio- and stereoselective synthesis of tetra- and triarylethenes by N-methylimidodiacetyl boron-directed palladium-catalysed three-component coupling

“…In addition, a palladium-catalysed oxidative alkoxycarbonylation with carbon monoxide in MeOH allowed the construction of a fully substituted α,β-unsaturated ester 13 63 . Finally, a phenanthrene product (14) was obtained via a Suzuki-Miyaura coupling/oxidative cyclization cascade 64 .…”

“…Platform synthesis is a powerful strategy to realize the synthesis of complex molecules in a programable and diversity-oriented format. In this regard, the advances of metal catalysis have inspired tremendous efforts towards modular tetraarylethene construction starting from alkenes [11][12][13][14][15][16][17] or alkynes [18][19][20][21][22][23][24][25][26] . Nevertheless, lengthy synthetic operations, the poor functional group tolerance arising from the participation of organolithium or Grignard reagents, and the often-encountered poor regioselectivity strongly limits their practical application.…”

Stereo‐Defined Synthetic Route to (E)‐ and (Z)‐Tamoxifen Derived from(E)‐1‐Bromo‐2‐iodoalkenes.

“…Our initial experiment utilizing between ( E )‐1‐bromo‐2‐iodoalkene 1 and tributyl(phenyl)tin was performed in the presence of CuTC and PPh 3 that was effective mediators for chemo‐selective cross‐coupling in our previous report (Table , entry 1) . However, the chemical yield of desired adduct 2 resulted in miserable 10% along with numerous 53% yield of side‐products 3 that arose from problematic beta‐halogen elimination .…”

“…selective cross-coupling in our previous report (Table 1, entry 1). [12] However, the chemical yield of desired adduct 2 resulted in miserable 10% along with numerous 53% yield of side-products 3 that arose from problematic beta-halogen elimination. [13] On the other hand, when the PPh 3 was absent in entry 2, the CuTC yielded 2 in higher 20% and decreased 3 to 20%.…”

Metallaphotoredox‐Enabled Intermolecular Carbobromination of Alkynes with Alkenyl Bromides

“…Selective dehalogenation of bromide 3 with TMEDA/NaBH 4 in the presence of Pd catalyst to give 1,3‐dienes in 94% yield ( 50 ) [17] . Several C−C construction reactions could be feasibly achieved by utilizing the bromo group, including cyanation ( 51 ), [18] Sonogashira coupling ( 52 ), [19] Negishi coupling with organozinc ( 53 ), [20] and Suzuki‐Miyaura coupling with boronic acid ( 54 ), [21] furnishing corresponding functionalized dienes in a straightforward way. In the presence of base, 3 underwent easily β‐Br elimination to furnish enyne 55 in 99% yield [22] .…”