Synthesis and Oxidation Catalysis of [Tris(oxazolinyl)borato]cobalt(II) Scorpionates
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![Chemistry Publications Chemistry 6-2016 Synthesis and xidation Catalysis of [Tris(oxazolinyl)borato]cobalt(II) Scorpionates Regina R.](/docs-images/90/102610900/images/1-1.jpg "Reinig Iowa State University and Ames Laboratory Debabrata Mukherjee Iowa State University Zachary B.")
1 Chemistry Publications Chemistry Synthesis and xidation Catalysis of [Tris(oxazolinyl)borato]cobalt(II) Scorpionates Regina R. Reinig Iowa State University and Ames Laboratory Debabrata Mukherjee Iowa State University Zachary B. Weinstein Iowa State University and Ames Laboratory Weiwei Xie Iowa State University and Ames Laboratory Toshia Albright Iowa State University See next page for additional authors Follow this and additional works at: Part of the Inorganic Chemistry Commons, and the Materials Chemistry Commons The complete bibliographic information for this item can be found at chem_pubs/1010. For information on how to cite this item, please visit howtocite.html. This Article is brought to you for free and open access by the Chemistry at Iowa State University Digital Repository. It has been accepted for inclusion in Chemistry Publications by an authorized administrator of Iowa State University Digital Repository. For more information, please contact
2 Synthesis and xidation Catalysis of [Tris(oxazolinyl)borato]cobalt(II) Scorpionates Abstract The reaction of CoCl2 THF and thallium tris(4,4-dimethyl-2-oxazolinyl)phenylborate (TlToM) in tetrahydrofuran (THF) provides ToMCoCl (1) in 95 yield; however, appropriate solvents and starting materials are required to favor 1 over two other readily formed side-products, (ToM)2Co (2) and {HToM}CoCl2 (3). ESR, MR, FTIR, and UV/Vis spectroscopies were used to distinguish these cobalt(ii) products and probe their electronic and structural properties. Even after the structures indicated by these methods were confirmed by X-ray crystallography, the spectroscopic identification of trace contaminants in the material was challenging. The recognition of possible contaminants in the synthesis of ToMCoCl in combination with the paramagnetic nature of these complexes provided impetus for the utilization of X-ray powder diffraction to measure the purity of the ToMCoCl bulk sample. The X-ray powder diffraction results provide support for the bulk-phase purity of ToMCoCl in preparations that avoid 2 and 3. Thus, 1 is a precursor for new [tris(oxazolinyl)borato]cobalt chemistry, as exemplified by its reactions with KtBu and aac to give ToMCotBu (4) and ToMCoAc (5), respectively. Compound 5 is a catalyst for the oxidation of cyclohexane with meta-chloroperoxybenzoic acid (mcpba), and the rate constants and selectivity for cyclohexanol versus cyclohexanone and ε-caprolactone were assessed. Keywords Scorpionates, xazolines, Cobalt, Structure elucidation, xidation Disciplines Chemistry Inorganic Chemistry Materials Chemistry Comments This is the peer reviewed version of the following article: Reinig, Regina R., Debabrata Mukherjee, Zachary B. Weinstein, Weiwei Xie, Toshia Albright, Benjamin Baird, Tristan S. Gray et al. "Synthesis and xidation Catalysis of [Tris (oxazolinyl) borato] cobalt (II) Scorpionates." European Journal of Inorganic Chemistry 2016, no (2016): , which has been published in final form at DI: /ejic This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. Authors Regina R. Reinig, Debabrata Mukherjee, Zachary B. Weinstein, Weiwei Xie, Toshia Albright, Benjamin Baird, Tristan S. Gray, Arkady Ellern, Gordon J. Miller, Arthur H. Winter, Sergey L. Bud'ko, and Aaron D. Sadow This article is available at Iowa State University Digital Repository:
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4 FULL PAPER Tl + CoCl 2 THF TlTo M THF r.t., overnight -TlCl Co Cl (1) 1 95 ν Intensity (scaled) UV-vis Absorption spectra wavelength (nm) To M CotBu HTo M CoCl 2 To M 2Co To M CoCl μ μ μ μ 2
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κ $7 7 ;<:=,<=:. /7:5; :.*-24A <1. $7 420*6- *88*:.6<4A -7.; 67< ;=887:< ;2@,77:-26*<. 8;.=-7 ;*6-?2,1<A8./2:;< :7?5.<*4,7587=6-; 26,76<:*;< <7 κ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
6 FULL PAPER 2 Tl + CoCl 2 THF THF r.t., overnight -2 TlCl B Co B 2 98 ν μ μ (2) 4
7 FULL PAPER *6-*67<1.:;8.,2.;?12,1?*;4*<.:2-.6<2/2.-*;#7 7, ; ? #1=; 7 4 # 2; <1. 8:./.::.- ;<*:<260 5*<.:2*4 /7:.6<:A 26<7,7+*4<,1.52;<:A 7/ <:2; 7@*B7426A4 +7:*<.420*6-; &2<1 2;74*+4. /=44A,1*:*,<.:2B.- *6- ;8.,<:7;,782,*44A *6-*6*4A<2,*44A8=:.# *6-?.<.;<.-2<;:.*,<2>2<A 26 1*42-. ;=+;<2<=<276; <7 8:.8*:. #7 7 = *6- #7 7,!.*,<276 7/ #7 7 4 *6- = 26 <.<:*1A-:7/=:*6:.*-24A8:7>2-.;#7 7 =.9 #1.:.*,<2767/ *6-( < ) 48:7>2-.;* < ;A6<1.;2; 7/,7587=6-.9 4<.:6*<2>.4A 2#7 *6-7 4 :.*,<26?.<5.<1A4.6.,147:2-.<78:7>2-.,:A;<*4;7/ -2:.,<4A/:75<1.:.*,<27652@<=:. Co + [HEt 2]Cl Cl THF H 1 r.t., 0.5 h B Cl Co (3) Cl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ν 7/,7+*4<,77:-26*<.- 7@*B7426. *6-8:7<76*<.- 7@*B7426. :.;8.,<2>.4A 7587=6-?*; *4; ;826 7 *;; *; *06.<75.<:A.@8.:25.6<;<1*<26-2,*<.-*H.//7/ μ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o Cl + K tbu THF r.t., 12 h 1 Co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μ *< $6423.,7587=6-; #7 7 = =6-.:07.; * +:7*-<1.:5*44A26-=,.-;826<:*6;2<276*6-H.//2; μ *<,76;2;<.6<?2<1*47?;826;<*<. "!.,:A;<*442B*<276 7/ /:75 <74=.6.,774.- *< E C 8:7>2-.- ' :*A 9=*42<A,:A;<*4; *6- * ;2604.,:A;<*4 ' :*A -2//:*,<276 ;<=-A,76/2:5.- < <2<A 7/ *; #7 7 = 20=:. #1. 7E -2;<*6,.; *: : 26 <1* *--2<276 <1. 7 * ; 4.;; <1*6 < * #1. 7 *604.2; C *6-<12; 5
8 FULL PAPER (3.1,<,+.,89/, :.74:503),9<,,39/,2,9/>1.74:584- (3+ 4=(?4103,8 ",3+,7,+9/,72(1, $4 4 * (7, 51499,+(9 574)()0109> (9428/(;,),,342099,+-47*1(709> #,1,*9,+ 039,7(9420* +089(3*,8 A #,1,*9,+039,7(9420*(3.1,8 +, ",3+,7,+9/,72(1, $4 4 : (7, 51499,+(9 574)()0109> (9428/(;,),,342099,+-47*1(709> #,1,*9,+ 039,7(9420* +089(3*,8 A #,1,*9,+039,7(9420*(3.1,8 +, (*9 *(9(1>?,8 9/, 4=0+( *>*14/,=(3, 94 *>*14/,=(341 <09/ */14745,74=>),3?40* (*0+ 2! (89/,9,7203(14=0+(39.0;03.,6:0; 4-*>*14/,=(3415,7 *(9(1>89 (-9,7 / 9,(71> 89(.,8 4-9/, 7,(*9043 / 9/, 574+:*9 7( *>*14/,=(341 *>*14/,=(343, ε *(5741(*943, 08 <09/,6:0; 4-*>*14/,=( ,+5,7 $/08 8,1,*90;09> +,*7,(8,8 (8 9/, 7,(* *,,+8 (3+ ε *(5741(*943, , /, 7,(* ! (3+ *>*14/,=(343, :2,3, />+745,74=0+, (3+ ):9>1 />+745,74=0+, <,7, 9,89,+ (8 4=0+( /08 *(9(1>90* 97(38-472(9043 ):9 431> 2! (--47+,+ 9/, +,807,+ *43;,78043 *439741,=5,702,39 03 </0*/ *>*14/,=(3, (3+ 2! <,7, 20=,+ ( ,25,7(9:7, ;0+, +,9,*9()1, 6:(39090,8 4- *>*14/,=(341 *>*14/,=(343, 47 ε *(5741(*943, :79/,7247, (3/>+74: (3/>+74:8 4 * (8 4 * (7, 54471> 841:)1, :3+,7 9/,8, 7,(*9043 * (3+ 9/ *425( <09/ 4<,;,7 9/, 5(790(11> 841:)1, 8:85,3+,+ 2(9,70(18.0;,8 14<,7 (*90;09> ( ,7 8,1,*90;09> *425(7,+ 94 :3+,7 *425(7()1,* $4 ),99,7 0+,390-> 9/, 5(7(2,9,78 (884*0(9,+ <09/ 9/, 4=0+( *,88 9/, 7,(* =9:7, <( ,+ <09/ (106:498 (3(1>?,+ )> 94 +,9,7203, *43*,397( *>*14/,=(341 *>*14/,=(343, (3+ ε *(5741(*943, 3 ( 7,(*9043 <09/ 2 & ' 9/, *43*,397( *>*14/,=(341 7,(*/,8 ( 89,(+> 89(9, 203 $/, &*>*14/,=(341' ;8 902, 03 0.:7, *(3 ), -09 <09/ ,(7 1,(8986:(7,7,.7, " 94,6:(9043 & ' k1 k t k t [C 6H12]t = [C 6H12 ]0 e 1 e 2 (6) k 2 k1 $/, 7,(* $4 4 1 (3+ ( * 03 9,97(/>+74-:7(3 574;0+,8$4 4 * (8(10./9 5:751,*4147, /0./ 0841(9,+ >0,1+,6 4254:3+ <(8 */(7(*9,70?,+ )> (3+ " 85,*9748*45> $/, " 85,*97:2 *439(03,+ 3,< =(?4103>1 5/,3>1)47(9, 80.3(18 (3+ 9/, (*,9(9, 80.3(1 (55,(7,+ -(7 :5-0, $/, " 80.3(1 4- (55,(7,+ (9 552 </0*/ <(8 +4<3-0,1+ 7,1(90;,949/,80.3(18-47 (3+ THF Co Co Cl + aac (5) r.t., 24 h 1 -acl /, " 85,*97:2 ( 803.1, )(3+ *477, /, 4=(?4103, 897,9*/ , <(8 4)8,7;,+ (9 *2D 4254:3+ 08/0./ 8503 F,-- μ (8+,9,7203,+)> 9/, ;(38 2,9/4+ 7(> 6:(109> *7>89(18 <,7, 4)9(03,+ )> 7,*7>89(110?( ,39(3,(9D B 0.:7, $/, 4 ) (3*,8 (3+ A<,7,143.,79/(39/, 4 ) (3*,03 A (3+9/, (3*,8 <,7,( ,79/(303 (3+ 4)(19 (*,9(9, 08 :8,+ (8 (3 03+:8970(1 *(9(1> /, 4=0+( =>1,3, 94 9,7,5/9/(10* (*0+ & ' ( ,3 10.(3+ )(8,+ *4)(19 *4254:3+8 /(;, (184 ),,3 89:+0,+ 03 *>*14/,=(3, 4=0+( *>*14/,=(341 & +' 3 9/08 4=0+(9043 *(9(1>808 8,1,*90;09> -47 ( 803.1, 4=0+( *>*14/,=(341 7(9/,7 9/(3 4;,7 4=0+( *>*14/,=(343, 47 ε *(5741(*943, 08 +,807,+,8509, 9/, (39 741, 4- *4)( =0+(9043 */,20897> $5 4 )(8,+ *4254:3+8 <,7, 349,--,*90;, -47 *>*14/,=(3, 4=0+(9043 & ' 84 ( 89:+> 4- $4 4 *(8(34=0+(9043*(9(1>89574;0+,8(*425( /,5>7(?41>1)47(9,(3(14.:,8 { } 7429/08(3(1>808 9/,4)8,7;,+7(9,*4389( =0+( *>*14/,=(3, 94 *>*14/,=( (3+ 4=0+( *>*14/,=( (;,7(., 4- -4:7,=5,702,398 8,, # ;0+:(1 *:7;,8 $/:8 8,1,*90;09> -47 *>*14/,=( :*9043 *42,8 03 ( 1(7., 5( /, /0./ & '030 (8,+ 43 9/,8, 7,8:198 <, (7, *:77,391> 89:+>03. 7,(*9043 * ,25,7(9:7, 841;,39 541(709> 6
9 FULL PAPER Concentration (M) time (min) To M CoAc, 0.16 mm CyH [] > CyH + Cy= + Caprolactone C 6 H 11 H C 6 H 10 2 C 6 H 10 νν μ νν ν μ 7
10 FULL PAPER νν ν ν μ νν ν ν μ 8
11 FULL PAPER 9
12 FULL PAPER Entry for the Table of Contents xazolinylborato scorpionates: ESR G X-ray To M CoCl 10
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