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The monoalkylation of acetonitrile by primary alcohols was achieved in a one-pot sequence in the presence of iridium catalysts. A diversity of nitriles has been obtained from aryl- and alkyl-methanols in excellent yield.

As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of the ring expansion of cyclic 2-hydroxymethyl amines induced by diethylaminosulfur trifluoride (DAST) to produce cyclic β-fluoro amines was studied as well as the enantioselectivity of the process.

The first iridium‐catalyzed intramolecular alkylation ofnitriles with primary and secondary alcohols through hydrogen transfer is described. This reaction allows access to precursors of biologically active arylmethylamines.

An iridium-catalyzed hydrogen transfer has been developed in the presence of p-benzoquinone, allowing the synthesis of a diversity of substituted benzofurans, benzothiophenes, and indoles from substituted benzylic alcohols.

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I n the Supporting Information of this paper, the presence of solvents was observed in the spectra of 8, 12e, 12f, 15a, and 16c. Original products were found in our library, and the spectra were rerecorded and have been replaced for compounds 8, 12e,f, 15a, and 16c.The spectra for 2, 6, 9, 10, 11b,c, 12c,d, 13a,b, 14a,e,f, 15b,c−e, 16a,b, 17b−d, 18b, 20b−d, 21a,b, and 22a−d were found to be edited to remove solvents and impurities. Original products were located and purified, and the spectra were recorded and have been replaced for all of the above compounds except for 2, 18b, and 22b,d, which were resynthesized and new spectra are provided. In addition, for 16a, the original FID file was located and the correct spectra are provided. Except as stated below, yields remained as previously reported.In Scheme 4, compound 2 (volatile) was resynthesized, and the yield was found to be 53%.In Scheme 6, compound 18b was resynthesized, and the yield was found to be 62%. For compound 18b, a note should be added: 48 h at 110 °C were necessary to perform a complete reaction.In Scheme 7, compounds 22b and 22d were resynthesized. The yield for 22b was found to be 65%, and the yield for 22d was found to be 62%. ■ ASSOCIATED CONTENT * S Supporting InformationRevised file containing experimental data and spectra. This material is available free of charge via the Internet at http:// pubs.acs.org.

In the Supporting Information of the original article, [1]