O-Carboranylene versus Phenylene Backbones in Cyclization Reactions of 1,2 Diketones with Hydrosilanes

Kuldeep Jaiswal, Karina Chulsky, Mark Gandelman, Roman Dobrovetsky*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The difference in reactivity of 1,2-dibenzoyl-o-carborane (2) and its analogue with an aromatic backbone and two C6F5electron withdrawing groups, C6H4(CO(C6F5))2(5), in cyclization reactions with R3SiH (R = Et, Ph (a)) with or without a catalytic amount of B(C6F5)3was studied. In contrast to the reaction of 2 with R3SiH, which directly leads to the cyclic hydrofurane products 3 and 4, 5 and R3SiH do not react without a catalytic amount of B(C6F5)3. However, in the presence of a catalytic amount of B(C6F5)3, 5 reacts with R3SiH forming through hydrofurane-type products 9, 9a, isobenzofuran 6. 2, on the other hand, reacts with R3SiH in the presence of a catalytic amount of B(C6F5)3giving stable products 10, 10a. 10, 10a in the presence of B(C6F5)3transform over time to a mixture of diastereomers 3′, 3a′. The mechanisms leading to these reactions are proposed on the basis of experimental and computational investigation.

Original languageEnglish
Pages (from-to)4232-4237
Number of pages6
JournalOrganometallics
Volume39
Issue number23
DOIs
StatePublished - 14 Dec 2020

Funding

FundersFunder number
Ministry of Science, Technology and Space65692
Israel Science Foundation237/18

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