Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

• Xiaowei Li,
• Xiaolin Shi,
• Xiangqian Li and
• Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

Cobalt-catalyzed directed C–H alkenylation of pivalophenone N–H imine with alkenyl phosphates

• Wengang Xu and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2018, 14, 709–715, doi:10.3762/bjoc.14.60

• groups into the ortho position of functionalized arenes has attracted significant attention because of the synthetic versatility of alkenyl groups. The C–H alkenylation has been achieved most extensively by way of the dehydrogenative Heck-type reaction of olefins [7][8][9]. Meanwhile, the hydroarylation

Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides

• Tao Fan,
• Wei-Dong Meng and
• Xingang Zhang

Beilstein J. Org. Chem. 2017, 13, 2610–2616, doi:10.3762/bjoc.13.258

• , Shanghai 200032, China 10.3762/bjoc.13.258 Abstract An efficient palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides has been developed. The reaction proceeds under mild reaction conditions with high efficiency and excellent functional group tolerance, even towards

• formyl and hydroxy groups. Preliminary mechanistic studies reveal that a secondary trifluoromethylated alkyl radical is involved in the reaction. Keywords: alkenes; cross-coupling; Heck-type reaction; palladium; secondary trifluoromethylated alkyl bromides; Introduction With the increasing number of

• fluoroalkyl metal species [18][19][20][21][22][23][24]. Recently, we reported a palladium-catalyzed Heck-type reaction of fluoroalkyl bromides, representing an efficient and straightforward alternative to access fluoroalkylated alkenes [25][26][27]. Preliminary mechanistic studies reveal that a fluoroalkyl

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

• Markus Leibeling and
• Daniel B. Werz

Beilstein J. Org. Chem. 2013, 9, 2194–2201, doi:10.3762/bjoc.9.258

• delivered the best results with yields of up to 89%. For the reaction mechanism we assume that the palladium(0) inserts into the C(sp2)–Br bond to form a Pd(II) species. A sequence of two carbopalladation reactions form a triene system which is able to cyclize by a Heck-type reaction, a 6π

Intramolecular carbonickelation of alkenes

• Rudy Lhermet,
• Muriel Durandetti and
• Jacques Maddaluno

Beilstein J. Org. Chem. 2013, 9, 710–716, doi:10.3762/bjoc.9.81

• skeleton was achieved by using NiBr2bipy catalysis. Keywords: alkenes; carbometallation; carbonickelation; cyclization; Heck-type reaction; nickel catalysis; Introduction Carbometalation is a reaction involving the addition of an organometallic species to a nonactivated alkene or alkyne to form a new

• work, we have shown that the NiBr2bipy complex can be used to catalyze an intramolecular Heck-type reaction in the absence of any additional base. This glove-box-free procedure occurs using 20% of NiBr2bipy and does not require the handling of air- or moisture-sensitive reagents. Thus, this single

Iron-containing mesoporous aluminosilicate catalyzed direct alkenylation of phenols: Facile synthesis of 1,1-diarylalkenes

• Satyajit Haldar and
• Subratanath Koner

Beilstein J. Org. Chem. 2013, 9, 49–55, doi:10.3762/bjoc.9.6

• synthesis. Thus, the development of simple methods concerning such vinylation reactions of phenols always remains an important process. Mizoroki–Heck-type reaction could be considered as an efficient procedure for the synthesis of such vinylated phenols [18][19]. There are a number of reports available in

• the literature that involve Pd-catalyzed cross coupling reactions of various aryl halides with different olefins. However, the major drawback of the Mizoroki–Heck-type reaction in the synthesis of 1,1-disubstituted olefins rests on its poor selectivity toward the formation of α-products [20][21][22

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• easily removed from IV by the anion formed from the initial palladium salt with generation of the 3-indolyl-palladium complex V, which evolves a Heck-type reaction to give the 3-alkenylindoles 1. Conversely, the deprotonation of the C-3 position is difficult in acidic medium, favoring the transfer of

The arene–alkene photocycloaddition

• Ursula Streit and
• Christian G. Bochet

Beilstein J. Org. Chem. 2011, 7, 525–542, doi:10.3762/bjoc.7.61

• [56] and also demonstrated that the meta photocycloaddition products containing a methoxy group at position 1 can be converted in a Heck-type reaction [57][58]. The intermediate palladium σ-complex, formed by insertion, opens the cyclopropane ring and arylated bicyclo[3.2.1]octane derivatives are