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Issue 36, 2018
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Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds

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Abstract

We report here reactions between the N-adamantyliminopyrolyl ligand 2-(AdN[double bond, length as m-dash]CH)–C4H3NH (L–H) and alkali metal hexamethyldisilazides [MN(SiMe3)2] (M = Li, Na and K) to afford the dimeric [{2-(AdN[double bond, length as m-dash]CH)–C4H3NLi(THF)}2] (1), [{2-(AdN[double bond, length as m-dash]CH)–C4H3N}{Na(THF)1.5}2] (2) and polymeric [{2-(AdN[double bond, length as m-dash]CH)–C4H3NK(THF)}n] (3) complexes at ambient temperature. A one-pot reaction between L–H, [KN(SiMe3)2] and alkaline earth metal diiodide (AeI2) in a 2 : 2 : 1 molar ratio, which resulted in the formation of a heteroleptic Ae metal complex [κ2-{2-(AdN[double bond, length as m-dash]CH)–C4H3N}2Ae(THF)2] [Ae = Mg (4), Ca (5)], is also reported. The solid-state structures of complexes 1, 3 and 4 were established through single-crystal X-ray diffraction analysis. The alkali and alkaline earth metal complexes 1–5 were utilised as precatalysts for the catalytic hydroboration of pinacolborane (HBpin) with aldehydes and ketones, and potassium complex 3 was identified as a competent catalyst under mild conditions. Additionally, cyanosilylation of carbonyl compounds was explored with trimethylsilyl cyanide and aldehydes/ketones, using the alkali metal precatalyst 3 under mild conditions. In both catalytic processes, the potassium catalyst 3 exhibited high tolerance towards a number of functional groups.

Graphical abstract: Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds

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Supplementary files

Article information


Submitted
18 May 2018
Accepted
16 Jul 2018
First published
17 Jul 2018

Dalton Trans., 2018,47, 12613-12622
Article type
Paper

Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds

A. Harinath, J. Bhattacharjee, H. P. Nayek and T. K. Panda, Dalton Trans., 2018, 47, 12613
DOI: 10.1039/C8DT02032A

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