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Expanding the limits of catalysts with low-valent main-group elements for the hydroboration of aldehydes and ketones using [LSn(II)][OTf] (L = aminotroponate; OTf = triflate)

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Abstract

A triflatostannylene [LSn(II)][OTf] (2) is reported here as an efficient catalyst with low-valent main-group element for the hydroboration of aldehydes and ketones (L = aminotroponate). Using 0.025–0.25 mol% of compound 2, hydroboration of various aldehydes and ketones is accomplished in 0.13–1.25 h at room temperature; the aliphatic aldehydes show an impressive TOF of around 30 000 h−1. DFT calculations are performed to explore the mechanistic aspects of this reaction suggesting that the reaction proceeds via a stepwise pathway with hydridostannylene [LSn(II)H] (2a) as the active catalyst and the H atom transfer from the Sn–H bond to the carbonyl carbon being the rate determining step.

Graphical abstract: Expanding the limits of catalysts with low-valent main-group elements for the hydroboration of aldehydes and ketones using [L†Sn(ii)][OTf] (L† = aminotroponate; OTf = triflate)

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Publication details

The article was received on 12 Jul 2018, accepted on 12 Nov 2018 and first published on 15 Nov 2018


Article type: Paper
DOI: 10.1039/C8DT02857E
Citation: Dalton Trans., 2019, Advance Article
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    Expanding the limits of catalysts with low-valent main-group elements for the hydroboration of aldehydes and ketones using [LSn(II)][OTf] (L = aminotroponate; OTf = triflate)

    M. K. Sharma, M. Ansari, P. Mahawar, G. Rajaraman and S. Nagendran, Dalton Trans., 2019, Advance Article , DOI: 10.1039/C8DT02857E

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