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Stoichiometric and catalytic carbon-...

Preshlock, Sean Michael.

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Stoichiometric and catalytic carbon-hydrogen borylations of arenes.

紀錄類型:	書目-語言資料,印刷品 : Monograph/item
正題名/作者:	Stoichiometric and catalytic carbon-hydrogen borylations of arenes./
作者:	Preshlock, Sean Michael.
面頁冊數:	269 p.
附註:	Source: Dissertation Abstracts International, Volume: 74-12(E), Section: B.
Contained By:	Dissertation Abstracts International74-12B(E).
標題:	Chemistry, Organic. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3593478
ISBN:	9781303363306

Stoichiometric and catalytic carbon-hydrogen borylations of arenes.
Preshlock, Sean Michael.

Stoichiometric and catalytic carbon-hydrogen borylations of arenes. - 269 p.

Source: Dissertation Abstracts International, Volume: 74-12(E), Section: B.

Thesis (Ph.D.)--Michigan State University, 2013.

Regioselective catalytic transformation of carbon-hydrogen bonds to other functional groups represents a long-standing challenge in homogeneous and heterogeneous catalysis. The Ir-catalyzed C-H activation/borylation has emerged as a useful method for synthesizing various aryl and heteroaryl boronic esters with regiochemistry complimentary to traditional methods and tolerant of various functional groups. The steric dominance of C-H activation/borylation has allowed for the synthesis of new aromatic building blocks which were previously unaccessible or hard to synthesize.

ISBN: 9781303363306Subjects--Topical Terms:

516206
Chemistry, Organic.

Stoichiometric and catalytic carbon-hydrogen borylations of arenes.
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100 1 $a Preshlock, Sean Michael. $3 2094040
245 1 0 $a Stoichiometric and catalytic carbon-hydrogen borylations of arenes.
300 $a 269 p.
500 $a Source: Dissertation Abstracts International, Volume: 74-12(E), Section: B.
500 $a Adviser: Milton R. Smith.
502 $a Thesis (Ph.D.)--Michigan State University, 2013.
520 $a Regioselective catalytic transformation of carbon-hydrogen bonds to other functional groups represents a long-standing challenge in homogeneous and heterogeneous catalysis. The Ir-catalyzed C-H activation/borylation has emerged as a useful method for synthesizing various aryl and heteroaryl boronic esters with regiochemistry complimentary to traditional methods and tolerant of various functional groups. The steric dominance of C-H activation/borylation has allowed for the synthesis of new aromatic building blocks which were previously unaccessible or hard to synthesize.
520 $a With the aid of high throughput experimentation (HTE), we designed reaction screens that would not only optimize Ir-catalyzed C-H borylation reactions for more challenging substrates, but also broaden the scope of this chemistry by assessing the efficiency and compatibility of the reactions as functions of precatayst, boron reagent, ligand, order of addition, temperature, solvent and substrate.
520 $a We then sought to apply these results to unprotected anilines which were inert under conventional Ir-catalyzed C-H borylation conditions. Building off a recent report from our research group that utilized a unique outer sphere directing effect to obtain ortho functionalized C-H borylation products from NBoc protected anilines, we investigated whether we could use HBPin as a traceless protecting/directing group for the borylation of primary anilines under more forcing conditions. Our attempts were successful and provided for a one-pot protection/deprotection procedure that used a lower catalyst loading and gave products in better to comparable yields than the NBoc protected borylation reaction.
520 $a Using an (&eegr;6-C6Me3H3)Ir(BPin) 3 as starting material, five-coordinate bisphosphine complexes can be synthesized by displacement of the &eegr;6-C6Me 3H3 with the incoming phosphine ligands. Using this method we have isolated the trans-Ir(PAr3F) 2BPin3 complex which is thought to be the active catalyst for the ortho-C-H directed borylation of benzoate esters first discovered by Miyaura. The trans-Ir(PAr3 F)2BPin3 complex is not catalytically competent with HBPin as borylating reagent. We have since been able to develop silylphosphine chelates (Figure 8) that are compatible with HBPin while retaining the unique selectivity shown with the Ir(PAr3F)2BPin 3 complex. Studies to further improve on the silylphosphine ligand design and extend the substrate scope are ongoing.
590 $a School code: 0128.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Inorganic. $3 517253
690 $a 0490
690 $a 0488
710 2 $a Michigan State University. $b Chemistry - Doctor of Philosophy. $3 2094041
773 0 $t Dissertation Abstracts International $g 74-12B(E).
790 $a 0128
791 $a Ph.D.
792 $a 2013
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3593478