Alcohols for alkylation! The first homogeneous‐catalyzed N‐alkylations of indoles with aliphatic alcohols proceed under transfer hydrogenation conditions. By the use of the Shvo catalyst and p‐toluenesulfonic acid (PTSA) this atom‐efficient reaction occurs highly selectively with water formed as the only byproduct (see scheme).

The amination of secondary alcohols to give tertiary amines in the presence of different in situ generated ruthenium catalysts has been investigated in detail. By applying a combination of [Ru3(CO)12] and N‐phenyl‐2‐(dicyclohexylphosphanyl)pyrrole as the catalyst, cyclic amines can be alkylated with different alcohols in high yield, whereas aliphatic amines gave transalkylation side products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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The monoamination of vicinal diols in the presence of in situ generated ruthenium catalysts has been investigated. Among the various phosphines tested in combination with [Ru(3)(CO)(12)], N-phenyl-2-(dicyclohexyl-phosphanyl)pyrrole showed the best performance. After optimization of the reaction conditions this system was applied to different secondary amines and anilines as well as a number of vicinal diols. With the exception of ethylene glycol, monoamination of the vicinal diols occurred selectively and the corresponding amino alcohols were obtained in good yields, producing water as the only side product.

Borrowing hydrogen catalysis for an environmentally benign N‐alkylation of indoles with alcohols is described in a joint effort by M. Beller, J. Williams, and co‐workers in their Communication on This novel procedure occurs through an unusual “borrowing hydrogen” methodology by use of the Shvo catalyst. The protocol is operationally simple and mechanistically involves an in situ transfer hydrogenation of the indole.