C–H bond halogenation catalyzed or mediated by copper: an overview

• Wenyan Hao and
• Yunyun Liu

Beilstein J. Org. Chem. 2015, 11, 2132–2144, doi:10.3762/bjoc.11.230

• ]. Halogenation of the alkene C(sp2)–H bond Beside the arene C–H bond, the alkene C–H is another typical C(sp2)–H bond. However, unlike the arene C–H bond, the alkene C–H bond tends to undertake difunctionalization via the cleavage of the π-bond in the presence of halogen source. Therefore, the halogenation of

Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides

• Akihiro Shimizu,
• Ryutaro Hayashi,
• Yosuke Ashikari,
• Toshiki Nokami and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2015, 11, 242–248, doi:10.3762/bjoc.11.27

• . Keywords: DMSO; electrosynthesis; epoxides; halohydrins; halogen cations; Introduction Alkene difunctionalization through three-membered ring halonium ion intermediates [1] is an important transformation in organic synthesis. Usually the halonium ions such as bromonium or iodonium ions are generated by

• . Recently, we reported that dimethyl sulfoxide (DMSO) can also be used to effectively stabilize halogen cations (Scheme 1) [22]. The pools of stabilized halogen cations enable alkene difunctionalization. We previously reported that the reaction of alkenes with DMSO-stabilized halogen cations such as Br+ and

Visible-light-induced bromoetherification of alkenols for the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans

• Run Lin,
• Hongnan Sun,
• Chao Yang,
• Youdong Yang,
• Xinxin Zhao and
• Wujiong Xia

Beilstein J. Org. Chem. 2015, 11, 31–36, doi:10.3762/bjoc.11.5

• reported that visible-light-induced photoredox catalysis could serve as a more environmental-friendly alternative reaction system to obtain Br2 in situ from CBr4, an oxidative quencher of photoredox catalyst [16][17][18][19][20][21][22]. Thus, as part of difunctionalization of alkenes, with our continuous

A reductive coupling strategy towards ripostatin A

• Kristin D. Schleicher and
• Timothy F. Jamison

Beilstein J. Org. Chem. 2013, 9, 1533–1550, doi:10.3762/bjoc.9.175

• substitution patterns [12][13][14][15]. Most recently, Sigman and colleagues have reported a palladium-catalyzed 1,4-difunctionalization of 1,4-butadiene with vinylboronic acid and vinyl triflate that can be used to rapidly access the skipped triene of ripostatin A [16]. We recognized that the C11 stereocenter

Homolytic substitution at phosphorus for C–P bond formation in organic synthesis

• Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 1269–1277, doi:10.3762/bjoc.9.143

• phosphorus always culminates in difunctionalization of a multiple bond. Therefore this methodology will find application in the synthesis of complex phosphines including bidentate ones. Radical substitution of halogen in organic halide with phosphorus will be an alternative to classical ionic substitution

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

• Kei Murakami and
• Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 278–302, doi:10.3762/bjoc.9.34

• ). The versatile 1,4-migration reactions were widely applicable for the 1,2-difunctionalization of arenes. In 2012, Gosmini reported similar cobalt-catalyzed arylzincation reactions of alkynes, which provided tri- or tetrasubstituted alkenes with high stereoselectivity [117]. Their catalytic system was

Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters

• Xiufang Ji,
• Zhiming Li,
• Quanrui Wang and
• Andreas Goeke

Beilstein J. Org. Chem. 2012, 8, 650–657, doi:10.3762/bjoc.8.72

• [18][19][20][21][22][23]. Ring-opening reactions of cyclobutanones are expected to be a valuable methodology for vicinal difunctionalization of double bonds. A prerequisite for this reaction to take place is the presence at C-2 of substituents capable of stabilizing the developing vicinal carbanion [6