Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

• Gwendal Grelier,
• Benjamin Darses and
• Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

• achievements reported in this area. Keywords: atom-economy; couplings; hypervalent iodine; oxidation; tandem reactions; Introduction Synthetic applications of the hypervalent iodine chemistry have grown exponentially in the last four decades as highlighted by several books and comprehensive reviews dedicated

Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent

• Elsa Deruer,
• Vincent Hamel,
• Samuel Blais and
• Sylvain Canesi

Beilstein J. Org. Chem. 2018, 14, 1203–1207, doi:10.3762/bjoc.14.101

• aromatic systems or cyclic ethers through a ring opening pathway. Keywords: hypervalent iodine; oxidation; sulfinates; sulfonation; sulfonium; Introduction Over the past few decades, hypervalent iodine reagents [1][2][3][4] have emerged as versatile and environmentally benign substitutes for heavy metal

2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

• Takayuki Yakura,
• Tomoya Fujiwara,
• Akihiro Yamada and
• Hisanori Nambu

Beilstein J. Org. Chem. 2018, 14, 971–978, doi:10.3762/bjoc.14.82

• the formation of the pentavalent iodine species from the corresponding trivalent iodine species might be the rate-determining step in the catalytic hypervalent iodine oxidation of 17 [70]. On the basis of the above results, a plausible mechanism for the oxidation catalyzed by the 2-iodobenzamides is

Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)

• Morifumi Fujita,
• Koki Miura and
• Takashi Sugimura

Beilstein J. Org. Chem. 2018, 14, 659–663, doi:10.3762/bjoc.14.53

• )-isomer. Keywords: 1,2-difunctionalization of alkenes; enantioselective synthesis; hypervalent iodine; oxidation; Findings Hypervalent aryl-λ3-iodanes have been widely used for metal-free oxidation with high selectivity in organic synthesis [1][2][3]. The reactivity of an aryl-λ3-iodane is controlled by

IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives

• Caifei Tang,
• Zhiming Li and
• Quanrui Wang

Beilstein J. Org. Chem. 2013, 9, 2629–2634, doi:10.3762/bjoc.9.298

• derivatives 5a–o. These incipient products undergo feasible Dimroth rearrangement to furnish the isolated [1,2,4]triazolo[1,5-c]pyrimidines 6a–o in moderate to high yields. Keywords: cyclization; hydrazones; hypervalent iodine; oxidation; rearrangement; [1,2,4]triazolo[1,5-c]pyrimidines; Introduction The

Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

• Sarah L. Harding,
• Sebastian M. Marcuccio and
• G. Paul Savage

Beilstein J. Org. Chem. 2012, 8, 606–612, doi:10.3762/bjoc.8.67

• dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of

• dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction. Keywords: dipolar cycloaddition; heterocycle; nitrile oxide; hypervalent iodine oxidation; pinacol boronic acid esters; Introduction Metal-mediated coupling reactions to form carbon–carbon

• , when forced, decomposition of the intermediate 5 with no detectible hydroximoyl chloride 6. Given that these reagents are oxidants such a result is perhaps not surprising. We then turned our attention to the direct oxidation of aldoximes using the mild conditions of hypervalent iodine oxidation and