This method offers a convenient alternative to the traditional benzylation and methylation of N-heterocycles with alkyl halides
. It is particularly useful in cases such as pyrroles which have a substantially more reactive anion compared to phenothiazine.
The second step involved quaternization of tertiaryamino groups with an alkyl halide
. The details of Q-POSS synthesis are provided in Appendix 1.
However, there are other synthetic routes, mainly based on alkylation of N'-mono- or di-substituted hydrazine derivatives with alkyl halides
[4, 6-8] (Scheme 1, B), or introducing a protecting group into commercially available alkyl hydrazines [4, 7-10] (Scheme 1, C).
Fu, "Cross-coupling of unactivated secondary alkyl halides
: room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides," Journal of the American Chemical Society, vol.
The Sr-mediated reaction produces high yields of both akylated and dialkylated adducts using alkyl halides
with easy handling.
(1999a), corrected for a printing error reported in Table 4.5 of this source for the class of alkyl halides
, mercaptans, sulphides and disulphides.
Chapters cover acids and bases; organic molecules and reactions of alkenes and alkynes; aromatic compounds; stereochemistry; alkyl halides
; alcohols, phenols, and ethers; aldehydes and ketones; carboxylic acids and derivatives; carbonyl alpha-substitution reactions; amines; structure determination; biomolecules; and metabolic pathways.
Currently, most of the metal-mediated reactions involve allylation or propargylation, and more recently, secondary alkyl halides
. However, the reactions did not work well with primary alkyl or aryl halides.