Formation of CC bond in solid phase synthesis using the heck reaction

Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes

“…To evaluate the effect of propolis components on cys-LTs release, cinnamic acid derivatives 1 and 3-5 in Brazilian green propolis were prepared as follows: synthesis of artepillin C (1) was initiated with the Mizoroki-Heck reaction 17 of iodide 14 18 with t-butyl acrylate in the presence of palladium acetate, tri-o-tolylphosphine and n-tetrabutylammonium chloride in aqueous N,Ndimethylformamide (DMF), 19,20 providing 15 in 81% yield. Treatment of the t-butyl ester with trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,6-lutidine followed by acidic work-up gave 1 in 71% yield.…”

Mizoroki–Heck Reactions: Modern Solvent Systems and Reaction Techniques

“…Diazonium salts were coupled in aqueous methanol in the presence of 2.0 mol% Pd(OAc) 2 [176]. Other groups applied 1,3-bis(diphenylphosphino)propane (dppp) in DMF-water in the presence of 3.0 mol% Pd(OAc) 2 [177], tetraphenylporphyrin (tpp) in DMF-water with 17 mol% Pd(OAc) 2 [178], Pd(dba) 2 (1.0-5.0 mol%) and P(o-tol) 3 in DMF-water [179], a palladacycle (0.001-0.50 mol%) in NMP-water, which even allowed the coupling of chloro aryls [151], or P(p-tol) 3 in DMF-water in the presence of Pd(OAc) 2 for the synthesis of monomers for coatings of electronic components [180]. The monomers are formed by Mizoroki-Heck reaction of 4-bromobenzocyclobutene with tetramethyldivinylsiloxane.…”

CC Bond‐Forming Reactions

“…It has been widely employed on a solid phase in various intra- [126,127,128,129] and intermolecular [28,30,127,130,131,132,133,134,135,136,137,138] versions. It is the coupling of an aryl or vinyl chloride [132], bromide [129,132,135,137,138,139], iodide [126,127,128,131,133,134,135,136,139], triflate [130], iodonium salt [30,140], or diazonium salt [29] with an alkene.…”

“…The most commonly used Pd source is the conveniently stable Pd(OAc) 2 [126,127,131,134,136,141]. However, Pd sources such as PdCl 2 (PhCN) 2 [141], Pd(PPh 3 ) 2 Cl 2 [128], and Pd(PPh 3 ) 4 [129] have been used.…”

“…Triethylamine [127,128,129,131], phosphines [126], K 2 CO 3 [131], and NaOAc [136] have been employed for this purpose. Often, a phosphine is used to facilitate ligand exchange and also to stabilize the active Pd species.…”