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Borane-induced ring closure reaction of oligomethylene-linked bis-allenes

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Abstract

The trimethylene-linked bis-allene 3a reacts with Piers' borane [HB(C6F5)2] by a hydroboration/allylboration sequence to generate the cyclization product 5a. Its pyridine adduct was isolated and characterized by X-ray diffraction. Compound 5a undergoes a typical frustrated Lewis pair 1,2-P/B alkene addition reaction with PPh3 to give the heterobicyclic bridged olefinic zwitterionic product 9a. The tetramethylene-linked bis-allene 3b and its phenylene annulated analogue 3c react with HB(C6F5)2 to give the analogous seven-membered ring products 5b,c under mild conditions. The cyclization product 5a undergoes a series of sequential allylboration reactions with two equivalents of allene followed by ring-closure to give the four-component coupling product 12a. It undergoes FLP addition to an exo-methylene group upon treatment with PPh3. Compound 12a is oxidatively converted to the boron-free alcohol.

Graphical abstract: Borane-induced ring closure reaction of oligomethylene-linked bis-allenes

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Article information


Submitted
03 Aug 2019
Accepted
17 Dec 2019
First published
18 Dec 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Borane-induced ring closure reaction of oligomethylene-linked bis-allenes

X. Tao, K. Škoch, C. G. Daniliuc, G. Kehr and G. Erker, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC03870A

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