Organometallic complexes of bulky, optically active, C3-symmetric tris(4S-isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate (ToP*)

Xu, Songchen; Magoon, Yitzhak; Reinig, Regina R.; Schmidt, Bradley M.; Ellern, Arkady; Sadow, Aaron D.

doi:10.1021/acs.organomet.5b00225

Title: Organometallic complexes of bulky, optically active, C₃-symmetric tris(4S-isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate (To^P*)

Journal Article · Thu Jul 16 00:00:00 EDT 2015 · Organometallics

DOI:https://doi.org/10.1021/acs.organomet.5b00225· OSTI ID:1227456

Xu, Songchen ^[1]; Magoon, Yitzhak ^[1]; Reinig, Regina R. ^[1]; Schmidt, Bradley M. ^[1]; Ellern, Arkady ^[1]; Sadow, Aaron D. ^[1]

Iowa State Univ., Ames, IA (United States)

A bulky, optically active monoanionic scorpionate ligand, tris(4S-isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate (To^P*), is synthesized from the naturally occurring amino acid l-valine as its lithium salt, Li[To^P*] (1). That compound is readily converted to the thallium complex Tl[To^P*] (2) and to the acid derivative H[To^P*] (3). Group 7 tricarbonyl complexes To^P*M(CO)₃ (M = Mn (4), Re (5)) are synthesized by the reaction of MBr(CO)₅ and Li[To^P*] and are crystallographically characterized. The ν_CO bands in their infrared spectra indicate that π back-donation in the rhenium compounds is greater with To^P* than with non-methylated tris(4S-isopropyl-2-oxazolinyl)phenylborate (To^P). The reaction of H[To^P*] and ZnEt₂ gives To^P*ZnEt (6), while To^P*ZnCl (7) is synthesized from Li[To^P*] and ZnCl₂. The reaction of To^P*ZnCl and KOtBu followed by addition of PhSiH₃ provides the zinc hydride complex To^P*ZnH (8). In this study, compound 8 is the first example of a crystallographically characterized optically active zinc hydride. We tested its catalytic reactivity in the cross-dehydrocoupling of silanes and alcohols, which provided Si-chiral silanes with moderate enantioselectivity.

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Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: CHE0955635; AC02-07CH11358

OSTI ID:: 1227456

Report Number(s):: IS-J-8725

Journal Information:: Organometallics, Vol. 34, Issue 14; ISSN 0276-7333

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 21 works

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CCDC 1419614: Experimental Crystal Structure Determination: JUTHEN : (tris((4S)-Isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate)-thallium Xu, Songchen; Magoon, Yitzhak; Reinig, Regina R. https://doi.org/10.5517/cc1jn70f The current record is supplemented by this dataset	dataset	August 2015
CCDC 1419615: Experimental Crystal Structure Determination: JUTHIR : Tricarbonyl-(tris((4S)-isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate)-manganese Xu, Songchen; Magoon, Yitzhak; Reinig, Regina https://doi.org/10.5517/cc1jn71g The current record is supplemented by this dataset	dataset	August 2015
CCDC 1419616: Experimental Crystal Structure Determination Xu, Songchen; Magoon, Yitzhak; Reinig, Regina R. https://doi.org/10.5517/cc1jn72h The current record is supplemented by this dataset	dataset	January 2015
CCDC 1419617: Experimental Crystal Structure Determination: JUTHUD : Chloro-(tris((4S)-isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate)-zinc Space Group: P 21 21 21 (19), Cell: a 12.3871(16)Å b 15.826(2)Å c 16.676(2)Å, α 90° β 90° γ 90° Xu, Songchen; Magoon, Yitzhak; Reinig, Regina R. https://doi.org/10.5517/cc1jn73j The current record is supplemented by this dataset	dataset	August 2015
CCDC 1419618: Experimental Crystal Structure Determination: JUTJAL : Hydrido-(tris((4S)-isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate)-zinc Xu, Songchen; Magoon, Yitzhak; Reinig, Regina https://doi.org/10.5517/cc1jn74k The current record is supplemented by this dataset	dataset	August 2015

Title: Organometallic complexes of bulky, optically active, C3-symmetric tris(4S-isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate (ToP*)

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