Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• -dihydronaphthalenes 47 with yields of up to 92%, as depicted in Scheme 21 [38]. The key aspect of the approach involved the simultaneous cleavage of dual C–C bonds and a single N–O bond, which was facilitated by the utilization of LiI/PPh3 as the photoredox system. Amination Anilines play important roles in both

Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes

• Thomas Schneider,
• Michael Keim,
• Bianca Seitz and
• Gerhard Maas

Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173

• -(1-phenylvinyl)indene 12 through an intramolecular iminium ion-induced 1,5-cyclization. The same cyclization type together with oxidative aromatization converts dihydronaphthalenes 16 into benzo[a]fluorenes 13. The stereochemistry of 12d can be explained by a stereoselective formation of trans-3,4

Oxidative radical ring-opening/cyclization of cyclopropane derivatives

• Yu Liu,
• Qiao-Lin Wang,
• Zan Chen,
• Cong-Shan Zhou,
• Bi-Quan Xiong,
• Pan-Liang Zhang,
• Chang-An Yang and
• Quan Zhou

Beilstein J. Org. Chem. 2019, 15, 256–278, doi:10.3762/bjoc.15.23

• produce the intermediate 18 followed by β-elimination to generate the desired product 13 [54][55][56]. In 2005, Yu et al. described a novel and efficient oxidative radical ring-opening and cyclization of MCPs 1 with benzenethiol (19) for the synthesis of 3-phenylsulfanyl-1,2-dihydronaphthalenes 20 in

• to generate intermediate 38 which is oxidized by Cu(II) to provide the CF3-substituted dihydronaphthalenes derivatives 31 along with releasing a proton [65][66]. The trifluoromethylthiolation of MCPs 1 with AgSCF3 was achieved by Shi et al. which proceeds through a sequence of radical addition, ring

• ''-hexamethylphosphorotriamide) as the additive in DMSO. With a similar oxidative radical ring-opening and cyclization strategy, our group developed a novel method for ring-opening and cyclization of MCPs 1 with ethers 40 afforded 2-substituted 3,4-dihydronaphthalenes 41 in moderate to excellent yields (Scheme 11) [68]. This

Reaction of selected carbohydrate aldehydes with benzylmagnesium halides: benzyl versus o-tolyl rearrangement

• Maroš Bella,
• Bohumil Steiner,
• Vratislav Langer and
• Miroslav Koóš

Beilstein J. Org. Chem. 2014, 10, 1942–1950, doi:10.3762/bjoc.10.202

• alcohols or a mixture of both, depending on the steric hindrance. However, the rearranged alcohols representing 1-methylene-2-substituted-1,2-dihydronaphthalenes F (analogues of intermediate B in Scheme 2) were unstable and decomposed to 1-methylnaphthalene (12) and the starting ketone 11 without the

Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes

• Ana M. Sanjuán,
• Alberto Martínez,
• Patricia García-García,
• Manuel A. Fernández-Rodríguez and
• Roberto Sanz

Beilstein J. Org. Chem. 2013, 9, 2242–2249, doi:10.3762/bjoc.9.263

• hydroxy(methoxy)-functionalized dihydronaphthalene derivatives is highly remarkable in the context of the observed reaction pathways for the cycloisomerizations of 1,6-enynes bearing a trisubstituted olefin. Keywords: catalysis; dihydronaphthalenes; gold; gold catalysis; hydroxycyclization; selectivity

β-Hydroxy carbocation intermediates in solvolyses of di- and tetra-hydronaphthalene substrates

• Jaya S. Kudavalli and
• Rory A. More O'Ferrall

Beilstein J. Org. Chem. 2010, 6, 1035–1042, doi:10.3762/bjoc.6.118

• led to the preparation of cis- and trans-1-trichloroacetoxy-2-methoxy-1,2-dihydronaphthalenes (3) which were stable enough to be isolated and purified (Figure 2). This allowed us to compare a ratio of rate constants for the solvolyses of these two isomers with the corresponding ratio for solvolyses of

• conclusion to be drawn from the measurements described above is that solvolysis of cis and trans 1-trichloroacetoxy-2-methoxy-1,2-dihydronaphthalenes (3) show an even larger advantage for reaction of the cis isomer, with kcis/ktrans = ~1800, than the acid-catalysed reaction of the corresponding dihydrodiols

• -chloro-2-hydroxy-1,2-dihydronaphthalenes (4) with the rate constant for the corresponding substrate lacking a hydroxy group (5) in Figure 3 shows that the hydroxy slows the rate by a factor of 860 in the case of the trans isomer and 1700 in the case of the cis. These rate retardations seem a little large

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

• Magnus Rueping and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6

• . Depending on the reaction conditions one observes either the corresponding dihydronaphthalenes or allenes as the main reaction products [92]. Catalytic propargylation of arenes (Prop-2-ynyl)arenes 84 are widely distributed structural motifs in organic chemistry due to the high synthetic value of the alkyne

Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles

• Dingqiao Yang,
• Ping Hu,
• Yuhua Long,
• Yujuan Wu,
• Heping Zeng,
• Hui Wang and
• Xiongjun Zuo

Beilstein J. Org. Chem. 2009, 5, No. 53, doi:10.3762/bjoc.5.53

• and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography. Keywords: chiral bisphosphine ligand; iridium catalyst; oxabicyclic alkenes; ring-opening reaction; Introduction Substituted dihydronaphthalenes are important molecules with