Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

• Chuanhua Qu,
• Run Huang,
• Yong Li,
• Tong Liu,
• Yuan Chen and
• Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

• 402160, China 10.3762/bjoc.17.193 Abstract Chemoselective sulfonylation and isonitrilation reactions for the divergent synthesis of valuable diarylmethyl sulfones and isonitrile diarylmethanes starting from easy-to-synthesize para-quinone methides (p-QMs) and commercially abundant p

• provides an efficient entry into the rapid assembly of various diarylmethyl sulfones and isonitrile diarylmethanes (Scheme 1C). Results and Discussion We commenced the study by using p-QMs 1a and TosMIC (2a) as model substrates to optimize the reaction conditions. As shown in Table 1, when 1a and 2a were

• spots were detected by TLC, but they quickly decomposed during column chromatography so that the target products could not be obtained (Scheme 3), which might be due to the easy-to-cleave nature of the p-toluenesulfonyl group. To further confirm the structure of the sulfonylated diarylmethanes, product

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• has been reported over the years. The most familiar methods to obtain substituted anthracenes include Friedel–Crafts reactions [17], Elbs reaction [18], aromatic cyclodehydration [19][20], Bradsher-type reactions from diarylmethanes [21][22][23], and, more recently, metal-catalyzed reactions with

Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

• Kimihiro Komeyama,
• Shunsuke Sakiyama,
• Kento Iwashita,
• Itaru Osaka and
• Ken Takaki

Beilstein J. Org. Chem. 2018, 14, 1413–1420, doi:10.3762/bjoc.14.118

• ) reagents, generated from the reaction of CrCl2 or CrCl3(thf)2 with phenyllithium [19][20], in the presence of allene 2a and aldehyde 3c provided diarylmethanes in 78–85% yields without the visible consumption of allene 2a (Scheme 10, reaction 1). Furthermore, in the absence of the CrCl3 catalyst, allene 2a

A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

• Anna Czarnecka,
• Emilia Kowalska,
• Agnieszka Bodzioch,
• Joanna Skalik,
• Marek Koprowski,
• Krzysztof Owsianik and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105

• (by electron-rich groups). This is leading to formyl-protected diarylmethanes with potential application in the synthesis of new pharmaceuticals and optoelectronic materials. This synthetic approach gives an access to a wide variety of functionalized ortho-1,3-dithianylaryl(aryl)methanes in 26–95

• % yields and is recommended for the substrates containing sulfur atoms, for which transition metal-induced reactions fail. Keywords: diarylmethanes; diarylmethanols; 1,3-dithiane; selective reduction; sodium cyanoborohydride; zinc iodide; Introduction In last decades, diarylmethanes, such as I–IV and

• reactions (e.g., Suzuki–Miyaura, Stille, Kumada, Hiyama or Negishi couplings) play a key role in the preparation of diarylmethanes. However, the reactions involving sulfur-containing moieties have not been reported yet (Scheme 1) [1]. It is noteworthy that under certain conditions, the Pd-catalyzed cross

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• diarylmethanes, acridine, xanthene, thioxanthene, etc. It was based on the generation of a benzotriazole-stabilized carbanion followed by oxidation of this carbanion by copper iodide to form a radical. Subsequent elimination of nitrogen followed by ring closure yielded phenanthridine (Scheme 2) [13][14]. In the

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

• intermediate which subsequently undergoes an intramolecular [1,3]- or [1,5]-hydride shift resulting in the desired diarylmethanes 9 in good yields. Electron donating and electron withdrawing functional groups of aldehyde moiety are tolerated in this reductive Friedel–Crafts alkylation procedure. However, there

• of carbon- and heteroatom-centered nucleophiles were effectively applied resulting numerous diarylmethanes and 3-substituted indoles. Moreover, this method could be extended to the C-glycosylation of 1-hydroxysugars and the products 28 were obtained in high yields and with remarkable anomeric ratios