Abstract:A cationic [(iminophosphine)nickel(allyl)] + complex was found to be sufficiently electrophilic to activate aldehydes and N-allylimines to undergo hydroboration with pinacolborane (HBpin) under mild reaction conditions. The catalyst displayed excellent selectivity toward aldehydes in the presence of ketones. A wide variety of functional groups were tolerated, includ- [a] I. 1877 ing halogens, NO 2 , CN, OMe, and alkenes for both aldehydes and imines. Electron-rich substrates were found to be significantly … Show more
“…However, no successful hydroboration of ketimine is reported by this catalyst. 42 Significantly, across all reports there have been limited examples of successful application of hydroboration strategies employing ketimine substrates; strongly indicating an ongoing need for more active/selective catalysts to be developed. The low abundance, high cost and toxicity of precious metal elements has prompted the catalytic community to focus heavily on an examination of the use of base metals in catalysis.…”
“…However, no successful hydroboration of ketimine is reported by this catalyst. 42 Significantly, across all reports there have been limited examples of successful application of hydroboration strategies employing ketimine substrates; strongly indicating an ongoing need for more active/selective catalysts to be developed. The low abundance, high cost and toxicity of precious metal elements has prompted the catalytic community to focus heavily on an examination of the use of base metals in catalysis.…”
“…Slightly sluggish reaction rates were observed in substrates with electron withdrawing groups. 100 In that same year, the Gade group reported an iron alkyl precatalyst (Fig. 4d) in the enantioselective hydroboration of N-alkyl imines.…”
Section: Base Metal Catalyzed Hydroboration Of Iminesmentioning
The catalytic hydroboration of imines, nitriles, and carbodiimides is a powerful method of preparing amines which are key syn-thetic intermediates in the synthesis of many value-added products. Imine hydroboration has...
“…His contribution opened up a new method for preparing several boron derivatives. [89][90][91][92][93] The innumerable catalytic solutions have been implemented over many years, starting with those based on transition metals, [94][95][96][97][98][99][100][101][102] through those utilizing rare-earth element complexes, [103][104][105][106][107][108] up to the main group species-catalyzed approaches. [109][110][111][112][113] Once more, our attention was drawn in particular to the procedures utilizing Earth-abundant s-block species.…”
Section: Hydroboration Of Unsaturated Carbon-heteroatom (O N) Moietiesmentioning
Hydroelementation enables a facile reduction or functionalization of several unsaturated systems, and thus activation of such bonds like B–H and Si–H is a powerful synthetic tool.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.