The 9-borataphenanthrene anion is easily accessed by deprotonation of a 9,10-dihydro-9-boraphenanthrene and its diverse reactivity is investigated. Alkylation occurs at the carbon atom adjacent to boron, and room temperature hydroboration occurs across the B=C bond. The π-manifold of the central BC ring coordinates to chromium in an η fashion while only the B=C unit binds η to gold, indicating versatility of the 9-borataphenanthrene anion as a ligand. Supporting calculations rationalize the reactivity and aromaticity is corroborated by nucleus-independent chemical shift (NICS) indices. 5 6 2
Funding
We are grateful to the Welch Foundation (Grant No. AA-1846) and the National Science Foundation for a CAREER Award (Award No. 1753025) for their generous support of this work. We also thank the ARC (FT16010007, DP20010013) for funding. We thank Dr. Sam Yruegas and Dr. Kevin K. Klausmeyer for assistance with X-ray crystallography and Dr. Xianzhong Xu for assistance with 1H{11B} and 11B{1H} NMR spectroscopy. NCI, Intersect, and La Trobe University are acknowledged for generous allocations of computing time.
Publication Date
2020-07-06Journal
Angewandte Chemie International EditionVolume
59Issue
28Pagination
7p. (p. 11470-11476)Publisher
Wiley-VCH Verlag GmbH & Co. KGaAISSN
1433-7851Rights Statement
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: Bartholome TA; Kaur A; Wilson D; Dutton J & Martin C (2020). The 9-borataphenanthrene anion. Angewandte Chemie - International Edition, 59(28), 11470-11476, which has been published in final form at http://doi.org/10.1002/anie.202002125. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
