Reaction of Dialumane Incorporating Bulky Eind Groups with Pyridines

The reaction of the bulky Eind-based dialumane, (Eind)HAl(μ-H)2AlH(Eind) (1) (Eind = 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl), with pyridines is described. When 1 was treated with pyridin...

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Main Authors:	Takahiro Murosaki, Ryoma Ohno, Tomohiro Agou, Daisuke Hashizume, Tsukasa Matsuo
Format:	Article
Language:	English
Published:	MDPI AG 2019-10-01
Series:	Inorganics
Subjects:	organoaluminum compounds aluminum hydrides pyridines hydroalumination deuterium labeling reaction
Online Access:	https://www.mdpi.com/2304-6740/7/11/129

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spelling	doaj-f2b1d03ff0584ad4b43d5f247f4626f22020-11-25T02:15:41ZengMDPI AGInorganics2304-67402019-10-0171112910.3390/inorganics7110129inorganics7110129Reaction of Dialumane Incorporating Bulky Eind Groups with PyridinesTakahiro Murosaki0Ryoma Ohno1Tomohiro Agou2Daisuke Hashizume3Tsukasa Matsuo4Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, JapanDepartment of Applied Chemistry, Faculty of Science and Engineering, Kindai University 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, JapanDepartment of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Naka-narusawa, Hitachi, Ibaraki 316-8511, JapanRIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama 351-0198, JapanDepartment of Applied Chemistry, Faculty of Science and Engineering, Kindai University 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, JapanThe reaction of the bulky Eind-based dialumane, (Eind)HAl(<i>μ</i>-H)<sub>2</sub>AlH(Eind) (<b>1</b>) (Eind = 1,1,3,3,5,5,7,7-octaethyl-<i>s</i>-hydrindacen-4-yl), with pyridines is described. When <b>1</b> was treated with pyridine (Py) in toluene, the Py adduct of aryldihydroalumane, Py→AlH<sub>2</sub>(Eind) (<b>2</b>), was initially formed. Then, the hydroalumination of Py took place to yield the Py-bound aryl(1,4-dihydropyrid-1-yl)hydroalumane, Py→AlH(1,4-dihydropyrid-1-yl)(Eind) (<b>3</b>). A similar reaction with a stronger Lewis base, 4-pyrrolidinopyridine (PPy), produced the stable PPy adduct, PPy→AlH<sub>2</sub>(Eind) (<b>4</b>). The resulting organoaluminum compounds have been fully characterized by NMR spectroscopy as well as X-ray crystallography. The reaction mechanism from <b>1</b> to <b>3</b> via <b>2</b> has been examined by deuterium labeling experiments using (Eind)DAl(<i>μ</i>-D)<sub>2</sub>AlD(Eind) (<b>1-<i>d</i><sub>4</sub></b>).https://www.mdpi.com/2304-6740/7/11/129organoaluminum compoundsaluminum hydridespyridineshydroaluminationdeuterium labeling reaction
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Takahiro Murosaki Ryoma Ohno Tomohiro Agou Daisuke Hashizume Tsukasa Matsuo
spellingShingle	Takahiro Murosaki Ryoma Ohno Tomohiro Agou Daisuke Hashizume Tsukasa Matsuo Reaction of Dialumane Incorporating Bulky Eind Groups with Pyridines Inorganics organoaluminum compounds aluminum hydrides pyridines hydroalumination deuterium labeling reaction
author_facet	Takahiro Murosaki Ryoma Ohno Tomohiro Agou Daisuke Hashizume Tsukasa Matsuo
author_sort	Takahiro Murosaki
title	Reaction of Dialumane Incorporating Bulky Eind Groups with Pyridines
title_short	Reaction of Dialumane Incorporating Bulky Eind Groups with Pyridines
title_full	Reaction of Dialumane Incorporating Bulky Eind Groups with Pyridines
title_fullStr	Reaction of Dialumane Incorporating Bulky Eind Groups with Pyridines
title_full_unstemmed	Reaction of Dialumane Incorporating Bulky Eind Groups with Pyridines
title_sort	reaction of dialumane incorporating bulky eind groups with pyridines
publisher	MDPI AG
series	Inorganics
issn	2304-6740
publishDate	2019-10-01
description	The reaction of the bulky Eind-based dialumane, (Eind)HAl(<i>μ</i>-H)<sub>2</sub>AlH(Eind) (<b>1</b>) (Eind = 1,1,3,3,5,5,7,7-octaethyl-<i>s</i>-hydrindacen-4-yl), with pyridines is described. When <b>1</b> was treated with pyridine (Py) in toluene, the Py adduct of aryldihydroalumane, Py→AlH<sub>2</sub>(Eind) (<b>2</b>), was initially formed. Then, the hydroalumination of Py took place to yield the Py-bound aryl(1,4-dihydropyrid-1-yl)hydroalumane, Py→AlH(1,4-dihydropyrid-1-yl)(Eind) (<b>3</b>). A similar reaction with a stronger Lewis base, 4-pyrrolidinopyridine (PPy), produced the stable PPy adduct, PPy→AlH<sub>2</sub>(Eind) (<b>4</b>). The resulting organoaluminum compounds have been fully characterized by NMR spectroscopy as well as X-ray crystallography. The reaction mechanism from <b>1</b> to <b>3</b> via <b>2</b> has been examined by deuterium labeling experiments using (Eind)DAl(<i>μ</i>-D)<sub>2</sub>AlD(Eind) (<b>1-<i>d</i><sub>4</sub></b>).
topic	organoaluminum compounds aluminum hydrides pyridines hydroalumination deuterium labeling reaction
url	https://www.mdpi.com/2304-6740/7/11/129
work_keys_str_mv	AT takahiromurosaki reactionofdialumaneincorporatingbulkyeindgroupswithpyridines AT ryomaohno reactionofdialumaneincorporatingbulkyeindgroupswithpyridines AT tomohiroagou reactionofdialumaneincorporatingbulkyeindgroupswithpyridines AT daisukehashizume reactionofdialumaneincorporatingbulkyeindgroupswithpyridines AT tsukasamatsuo reactionofdialumaneincorporatingbulkyeindgroupswithpyridines
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Reaction of Dialumane Incorporating Bulky Eind Groups with Pyridines

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