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Hydrogenation and Hydroamination Rea...

Mahdi, Tayseer.

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Hydrogenation and Hydroamination Reactions Using Boron-Based Frustrated Lewis Pairs.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Hydrogenation and Hydroamination Reactions Using Boron-Based Frustrated Lewis Pairs./
Author:	Mahdi, Tayseer.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2015,
Description:	231 p.
Notes:	Source: Dissertation Abstracts International, Volume: 77-07(E), Section: B.
Contained By:	Dissertation Abstracts International77-07B(E).
Subject:	Chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10016822
ISBN:	9781339498171

Hydrogenation and Hydroamination Reactions Using Boron-Based Frustrated Lewis Pairs.
Mahdi, Tayseer.

Hydrogenation and Hydroamination Reactions Using Boron-Based Frustrated Lewis Pairs. - Ann Arbor : ProQuest Dissertations & Theses, 2015 - 231 p.

Source: Dissertation Abstracts International, Volume: 77-07(E), Section: B.

Thesis (Ph.D.)--University of Toronto (Canada), 2015.

New main group systems that provide avenues for small molecule activation have been illustrated using frustrated Lewis pairs (FLPs) -- combinations of sterically encumbered Lewis acids and bases which cannot form adducts. The research presented herein expands the small molecule activation and transformation of FLPs using B(C6F5)3.

ISBN: 9781339498171Subjects--Topical Terms:

516420
Chemistry.

Hydrogenation and Hydroamination Reactions Using Boron-Based Frustrated Lewis Pairs.
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100 1 $a Mahdi, Tayseer. $3 3281012
245 1 0 $a Hydrogenation and Hydroamination Reactions Using Boron-Based Frustrated Lewis Pairs.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2015
300 $a 231 p.
500 $a Source: Dissertation Abstracts International, Volume: 77-07(E), Section: B.
500 $a Adviser: Douglas W. Stephan.
502 $a Thesis (Ph.D.)--University of Toronto (Canada), 2015.
520 $a New main group systems that provide avenues for small molecule activation have been illustrated using frustrated Lewis pairs (FLPs) -- combinations of sterically encumbered Lewis acids and bases which cannot form adducts. The research presented herein expands the small molecule activation and transformation of FLPs using B(C6F5)3.
520 $a Combination of the aryl amine tBuNHPh and B(C6 F5)3 under H2 at room temperature leads to its heterolytic splitting forming the complex [tBuNH 2Ph][HB(C6F5)3]. Exposing the salt to elevated temperatures is found to follow an alternative mechanism resulting in hydrogenation of the N-bound phenyl ring affording the isolable cyclohexylammonium salt [tBuNH2Cy][HB(C 6F5)3]. This finding is extended to include a series of N-phenyl amines, in addition to mono- and di-substituted pyridines, quinolines and several other N-heterocycles.
520 $a The reaction of B(C6F5)3 and H 2 with other substrates, namely ketones and aldehydes are also investigated. Catalytic hydrogenation of the carbonyl functional group is achieved in an ethereal solvent to give alcohol products. In these cases, the borane and ether behave as a FLP to activate H2 and effect the reduction. Similar reductions are also achieved in toluene using B(C6F5)3 in combination with cyclodextrins or molecular sieves. Reductive deoxygenation occurs in the particular case of aryl ketones.
520 $a Finally, the Lewis acid B(C6F5)3 is found to enable the intermolecular hydroamination of various terminal alkynes giving iminium alkynylborate complexes of the general formula [RPhN=C(CH 3)R1][R1C&equiv;CB(C6F 5)3]. The three-component reaction can also be performed catalytically, generating enamine products which are amenable to subsequent hydrogenation reactions giving their corresponding amines. The chemistry is expanded to intramolecular systems forming N-heterocyclic compounds. Furthermore, a FLP route to stoichiometric hydrophosphination of alkynes is developed.
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650 4 $a Inorganic chemistry. $3 3173556
650 4 $a Organic chemistry. $3 523952
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710 2 $a University of Toronto (Canada). $b Chemistry. $3 3178441
773 0 $t Dissertation Abstracts International $g 77-07B(E).
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791 $a Ph.D.
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856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10016822