Stable silylating reagents

A solution composition prepared by preconditioning a mixture of:

• (a) a precursor hydrosilane;
• and
• (b) a base comprising potassium hydroxide, a potassium alkoxide, a potassium silanolate, rubidium hydroxide, a rubidium alkoxide, a rubidium silanolate, cesium hydroxide, a cesium alkoxide, a cesium silanolate, a potassium amide, or a combination thereof;
• in
• (c) a preconditioning solvent comprising one or more tetrahydrofurans, wherein the preconditioning solvent comprises 2-methyl-tetrahydrofuran;
• in the absence of any heteroaromatic, olefinic, or acetylenic substrates capable of C—H silylation, or any alcohol substrates;
• wherein
• the solution composition contains a species formed by the preconditioning of the mixture of (a) and (b) in the preconditioning solvent, wherein the species is present in sufficient amount to exhibit an observable infrared absorption peak in an Si—H stretching region of an infrared spectrum, that infrared absorption peak being of lower energy than a corresponding Si—H absorption peak of the precursor hydrosilane, when evaluated under comparable conditions;
• and wherein
• (i) the solution composition comprises the preconditioning solvent comprising one or more tetrahydrofurans, wherein the preconditioning solvent comprises 2-methyl-tetrahydrofuran, and is free of any added heteroaromatic, olefinic, or acetylenic substrates capable of C—H silylation by the pre-conditioned mixture, or of any added alcohol substrates;
• (ii) the preconditioning comprises holding the mixture of combined hydrosilane and the base in the preconditioning solvent under conditions sufficient to produce the solution composition, which is capable of initiating measurable silylation of 1-methyl indole at a temperature of 45° C. or less with an induction period of less than 30 minutes;
• (iii) the precursor hydrosilane is of the Formula (I) or Formula (II):
• (R)3−mSi(H)m+1 (I)
• (R)3−m(H)mSi—Si(R)2−m(H)m+1 (II)
• where:
• m is independently 0, 1, or 2;
• and each R is independently optionally substituted C1-24 alkyl, optionally substituted C2-24 alkenyl, optionally substituted C2-24 alkynyl, optionally substituted C6-12 aryl, C3-12 heteroaryl, optionally substituted C7-13 alkaryl, optionally substituted C4-12 heteroalkaryl, optionally substituted C7-13 aralkyl, optionally substituted C4-12 heteroaralkyl, and, if substituted, the substituents are independently nitro, C1-C20 alkoxy, C5-C20 aryloxy, or halogen.