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Addition reactions and diazomethane capture by the intramolecular P–O–B FLP: tBu2POBcat

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Abstract

FLPs, R2POBcat (R = tBu 1, Mes 2), are readily derived from the reactions of the corresponding phosphine oxides, nBuLi and ClBcat. Despite the poor Lewis acidity of boron, these species react with PhOH, CO2, CS2, PhNCO, MesCNO, O2, 9,10-phenanthrenedione, and diazomethanes to effect FLP addition reactions affording a series of heterocycles. The reaction of 1 with EtO2CCHN2 gives the bicyclic product, EtO2CCHN2(tBu2POBcat)2. High-level DFT calculations reveal that these cyclization processes proceed via 1,1-addition to the terminal N of diazomethane followed by 1,2-boron-migration affording the five membered rings. The reaction of the EtO2CCHN2 derivative with the second equivalent of FLP 1 is attributed to less steric demands.

Graphical abstract: Addition reactions and diazomethane capture by the intramolecular P–O–B FLP: tBu2POBcat

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Article information


Submitted
27 Nov 2019
Accepted
10 Dec 2019
First published
10 Dec 2019

Dalton Trans., 2020, Advance Article
Article type
Paper

Addition reactions and diazomethane capture by the intramolecular P–O–B FLP: tBu2POBcat

D. Zhu, Z. Qu and D. W. Stephan, Dalton Trans., 2020, Advance Article , DOI: 10.1039/C9DT04560K

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