Catalytic S N Ar of Unactivated Aryl Chlorides ESI

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1 Eltron Supplmntry Mtrl (ESI) or CmComm. Ts journl s T Royl Soty o Cmstry 2014 Ctlyt S Ar o Untvt Aryl Clors ESI Tl o Contnts 1. Prour n Full Tl o Contons - Prour S1 - Intl solvnt srn (no tlyst) - Solvnt srn wt [CpRu(p-ymn)PF 6 ] tlyst - Atv srn - Ln srn wt [Ru(p-ymn)Cl 2 ] 2 2. Exprmntl Dtl n Prout Crtrston 3. Mss Sptromtry Clrton 4. Hl L Clulton Prour n Full Tl o ontons Prour S1: To r Sln tu unr 2 tmospr ws tlyst (67 μmol, 10 mol% rltv to lorotolun), nyrous, ss lorotolun (80 μl, 0.67 mmol), nyrous, ss morpoln (167 μl, 2.0 mmol) n nyrous, ss solvnt (1 ml). T rton vssl ws sl n t mxtur ws strr t t rton tmprtur or t tm nt ( C or 18 ). Atr t vn rton tm, smpl o t ru rton mxtur (200 μl) ws to CDCl 3 (0.7 ml) n 1 H-MR ws us to trmn t rton onvrson. Intl solvnt srn (no tlyst) Prour S1 ws ollow. Tl S1: Vrton n solvnt n t sn o tlyst. Convrsons trmn y 1 H-MR. H + Cl Ctlyst (10 mol%) Solvnt, Tmp. Tm, Atv Entry Ctlyst Solvnt Tmp. ( C) Tm Atv Convrson (%) 1 - MC Tolun THF EtH DMS Cyloxnon tnol

2 8-1-tnol DMI MP Cyloxnol Solvnt srn wt [CpRu(p-ymn)PF 6 ] tlyst Prour S1 ws ollow. Tl S2: Vrton n solvnt usn [CpRu(p-ymn)]PF 6 s t tlyst. Convrsons trmn y 1 H-MR. H + Cl Ctlyst (10 mol%) Solvnt, Tmp. Tm, Atv Entry Ctlyst Solvnt Tmp. ( C) Tm Atv Convrson (%) 1 [CpRu(p-ymn)]PF 6 p-xyln [CpRu(p-ymn)]PF 6 Cyloxnon [CpRu(p-ymn)]PF 6 Cyloxnol [CpRu(p-ymn)]PF 6 DMS [CpRu(p-ymn)]PF 6 DMI [CpRu(p-ymn)]PF 6 MP [CpRu(p-ymn)]PF 6 Bnzyl lool [CpRu(p-ymn)]PF 6 1-tnol Atv Srn Prour S1 ws ollow wt t ton o t tv (1 q mmol) Tl S3: Vrton n tv. Convrsons trmn y 1 H-MR. H + Cl Ctlyst (10 mol%) Solvnt, Tmp. Tm, Atv Entry Ctlyst Solvnt Tmp. ( C) Tm Atv Convrson (%) 1 [CpRu(p-ymn)]PF 6 1-tnol [CpRu(p-ymn)]PF 6 1-tnol C [CpRu(p-ymn)]PF 6 1-tnol K 2 C [CpRu(p-ymn)]PF 6 1-tnol Cs 2 C [CpRu(p-ymn)]PF 6 1-tnol K t Bu 0 6 [CpRu(p-ymn)]PF 6 1-tnol Et 3 21

3 7 [CpRu(p-ymn)]PF 6 1-tnol Pr 2 Et 20 8 [CpRu(p-ymn)]PF 6 1-tnol Mol. Svs 25 9 [CpRu(p-ymn)]PF 6 1-tnol Mol. Svs + Et 3 10 [CpRu(p-ymn)]PF 6 1-tnol Mol. Svs + Pr 2 Et Ln Srn wt [Ru(p-ymn)Cl 2 ] 2 Prour S1 ws ollow wt t ollown justmnts: n t pl o tlyst (67 μmol, 10 mol% rltv to lorotolun), [Ru(p-ymn)Cl 2 ] 2 (33 μmol, 5 mol% rltv to lorotolun) ws ; ln (200 μmol, 3 quvlnts rltv to Ru) ws ; rton ws nlys tr 18 ; 1- otnol (1 ml) ws t solvnt. Tl S4: Vrton n ln wt [Ru(p-ymn)Cl 2 ] 2 tlyst. Convrsons trmn y 1 H-MR. [Ru(p-ymn)Cl 2 ] 2 (5 mol%) H 1-tnol, Tmp, 18 + Cl Ln Entry Ln Prout Convrson (%) T = 150 o C T = 180 o C Entry Ln Prout Convrson (%) T = 150 o C T = 180 o C P F PCy P M P CF PP JonPos P 0 0 P(M) P 2 P PP P 2 P PP 2 2 P 2 P PP P 2 P PP P 2 P PP pp XATPHS Cy 2 P PCy Exprmntl Dtl n Prout Crtrston

4 M ' ' ' ' ' ' ' ' M Mtyl (ylopnt-1,3-n-1-yl)tt n Mtyl (ylopnt-1,4-n-1-yl)tt A soluton o soum ylopntnyl (2 M n THF, 6.45 ml) ws lut n THF (20 ml) n ropws to strr soluton o mtyl romott (1.22 ml, 12.9 mmol) n THF (10 ml) t -78 C. T mxtur ws strr or 3 t -78 C or CH 2 Cl 2 (20 ml) ws to ltt prptton o Br, w ws rmov y ltrton. T solvnt ws rmov unr ru prssur rom t ltrt to lv 1 : 1 mxtur o t ttl prouts s yllow ol, w ws us wtout urtr purton (1.78, quntttv); δ H (CDCl 3 ) (6H, m, H / // // ), 3.50 (6H, s, H / ), 3.29 (4H, m, H / ), 2.85 (4H, m, H / ); δ C (CDCl 3 ) (C / ), n (C / ), (C / // // ), 52.2 (C / ), 44.5 n 42.3 (C / ), 36.7 n 36.1 (C / ); m/z (HRMS + ) [M + H] + (C 8 H 11 2 rqurs ). Ru + j l PF 6 - m n Etyl (ylopntnyl)tt(p-ymn)rutnum(ii) xluoropospt, 2 A 1 : 1 mxtur o mtyl (ylopnt-1,3-n-1-yl)tt n mtyl (ylopnt-1,4-n-1-yl)tt (1.78, 12.9 mmol) ws ssolv n ry, ss (3 r tw yl) EtH (10.5 ml). 2 C 3 (312 m, 2.94 mmol) n [Ru(p-ymn)Cl 2 ] 2 (300 m, 0.49 mmol) wr n t mxtur ws strr unr ron t 75 C or 16. T mxtur ws lt to stn or t suprntnt ws nt rom rsul slts n ru n volum to 3.5 ml. An quous soluton o H 4 PF 6 (0.3 M, 7.0 ml) ws n t mxtur ws xtrt wt CH 2 Cl 2 (3 10 ml). T orn rtons wr omn, r ovr MS 4 n t solvnt ws rmov unr ru prssur to v rown ol. Purton y olumn romtorpy (sl, CH 2 Cl 2 : EtH 0 0.2% n 0.1% nrmnts) v t ttl ompoun s yllow ol (228 m, 45%); δ H (CDCl 3 ) 6.28 (4H, m, H / ), 5.55 (2H, m, H ), 5.46 (2H, m, H ), 4.18 (2H, q, J 7.0 Hz, H m ), 3.52 (2H, s, H ), 2.85 (1H, spt., J 7.0 Hz, H ), 2.42 (3H, s, H ), 1.32 (6H,, J 7.0 Hz, H ), 1.26 (3H, t, J 7.0 Hz, H n ); δ C (CDCl 3 ) (C l ), (C ), (C ), 95.1 (C j ), 87.2 (C ), 84.8 (C ), 81.7 (C ), 80.1 (C ), 60.8 (C m ), 32.6 (C ), 31.8 (C ), 22.7 (C ), 18.8 (C ), 13.6 (C n ); δ P (CDCl 3 ) (spt.); δ F (CDCl 3 ) (); m/z (HRMS + ) [M PF 6 ] + (C 19 H Ru rqurs ); R = 0.27 (sl, CH 2 Cl 2 : 5% EtH).

5 M ' ' ' ' ' ' ' ' ' M Mtyl 3-(ylopnt-1,3-n-1-yl)propnot n mtyl 3-(ylopnt-1,4-n-1-yl)propnot A soluton o soum ylopntnyl (2 M n THF, 6.45 ml) ws lut n THF (20 ml) n ropws to strr soluton o mtyl 3-romopropont (1.41 ml, 12.9 mmol) n THF (10 ml) t -78 C. T mxtur ws strr or 3 t -78 C or CH 2 Cl 2 (20 ml) ws to ltt prptton o Br, w ws rmov y ltrton. T solvnt ws rmov unr ru prssur rom t ltrt to lv 1 : 1 mxtur o t ttl prouts s yllow ol, w ws us wtout urtr purton (1.96, quntttv); δ H (CDCl 3 ) (6H, m, H / // // ), 3.63 (6H, s, H / ), 2.92 (4H, m, H / ), (4H, m, H / ), 2.57 (4H, t, H / ); δ C (CDCl 3 ) (C / ), n (C / ), (C / // // ), 52.0 (C / ), 47.3 n 44.2 (C / ), 34.7 n 34.1 (C / ), 26.9 n 26.1 (C / ); m/z (HRMS + ) [M + H] + (C 9 H 13 2 rqurs ). Ru + PF 6 m j l - n o Etyl 3-(ylopntnyl)propnot(p-ymn)rutnum(II) xluoropospt, 3 A 1 : 1 mxtur o mtyl 3-(ylopnt-1,3-n-1-yl)propnot n mtyl 3-(ylopnt-1,4-n-1- yl)propnot (1.96, 12.9 mmol) ws ssolv n ry, ss (3 r tw yl) EtH (10.5 ml). 2 C 3 (312 m, 2.94 mmol) n [Ru(p-ymn)Cl 2 ] 2 (300 m, 0.49 mmol) wr n t mxtur ws strr unr ron t 75 C or 16. T mxtur ws lt to stn or t suprntnt ws nt rom rsul slts n ru n volum to 3.5 ml. An quous soluton o H 4 PF 6 (0.3 M, 7.0 ml) ws n t mxtur ws xtrt wt CH 2 Cl 2 (3 10 ml). T orn rtons wr omn, r ovr MS 4 n t solvnt ws rmov unr ru prssur to v rown ol. Purton y olumn romtorpy (sl, CH 2 Cl 2 : EtH 0 0.2% n 0.1% nrmnts) v t ttl ompoun s yllow ol (230 m, 43%); δ H (CDCl 3 ) 6.29 (4H, m, H / ), 5.47 (2H, m, H ), 5.39 (2H, m, H ), 4.11 (2H, q, J 7.0 Hz, H n ), 2.83 (1H, spt., J 7.0 Hz, H ), 2.66 (2H, t, J 7.5 Hz, H ), 2.59 (2H, t, J 7.5 Hz, H l ), 2.40 (3H, s, H ), 1.31 (6H,, J 7.0 Hz, H ), 1.22 (3H, t, J 7.0 Hz, H o ); δ C (CDCl 3 ) (C m ), (C ), (C j ), (C ), 87.0 (C ), 84.6 (C ), 81.0 (C ), 80.0 (C ), 60.1 (C n ), 34.4 (C l ), 31.8 (C ), 22.8 (C ), 22.7 (C ), 18.8 (C ), 13.6 (C o ); δ P (CDCl 3 ) (spt.); δ F (CDCl 3 ) (); m/z (HRMS + ) [M PF 6 ] + (C 20 H Ru rqurs ); R = 0.27 (sl, CH 2 Cl 2 : 5% EtH).

6 H 2 ' ' ' ' ' ' ' ' ' H 2 3-(Cylopnt-1,3-n-1-yl)propnm n 3-(ylopnt-1,4-n-1-yl)propnm A soluton o soum ylopntnyl (2 M n THF, 2.56 ml) ws lut n THF (7 ml) n ropws to strr soluton o 3-loroproponm (550 m, 5.12 mmol) n THF (4 ml) t -78 C. T mxtur ws strr or 3 t -78 C or t rton tmprtur ws nrs to 20 C n t mxtur ws strr or urtr 14. T solvnt ws rmov unr ru prssur to v yllow sol. Purton y olumn romtorpy (sl, CH 2 Cl 2 : CH 3 H 0 1% n 0.1% nrmnts, ry lo) v 1 : 1 mxtur o t ttl ompouns s wt morpous sol (246 m, 35%); δ H (CDCl 3 ) (6H, m, H / // // ), 5.40 (4H, r s, H / ), 2.88 (4H, m, H / ), (4H, m, H / ), (4H, m, H / ); δ C (CDCl 3 ) n (C / ), n (C / ), (C / // // ), 43.4 n 41.4 (C / ), 35.7 n 35.1 (C / ), 26.3 n 25.6 (C / ); m/z (HRMS + ) [M + ] + (C 8 H 11 rqurs ); R = 0.16 (sl, CH 2 Cl 2 : 5% CH 3 H). Ru + PF 6 n/n' m H 2 j l - 3-(Cylopntnyl)propnm(p-ymn)rutnum(II) xluoropospt, 4 A 1 : 1 mxtur o 3-(ylopnt-1,3-n-1-yl)propnm n 3-(ylopnt-1,4-n-1-yl)propnm (210 m, 1.53 mmol) ws ssolv n ry, ss (3 r tw yl) EtH (3.4 ml). 2 C 3 (97 m, 0.92 mmol) n [Ru(p-ymn)Cl 2 ] 2 (94 m, 0.15 mmol) wr n t mxtur ws strr unr ron t 75 C or 16. T mxtur ws lt to stn or t suprntnt ws nt rom rsul slts n ru n volum to 1.4 ml. An quous soluton o H 4 PF 6 (0.15 M, 4.0 ml) ws n t mxtur ws xtrt wt CH 2 Cl 2 (3 5 ml). T orn rtons wr omn, r ovr MS 4 n t solvnt ws rmov unr ru prssur to v rown ol. Purton y olumn romtorpy (sl, CH 2 Cl 2 : EtH 0 3% n 0.1% nrmnts) v t ttl ompoun s yllow ol (85 m, 55%); δ H (CDCl 3 ) 6.82 (1H, r s, H n ), 6.33 (1H, r s, H n ), 6.25 (4H, m, H / ), 5.42 (2H, m, H ), 5.36 (2H, m, H ), 2.82 (1H, spt., J 7.0 Hz, H ), 2.62 (2H, t, J 7.2 Hz, H ), 2.46 (2H, t, J 7.2 Hz, H l ), 2.38 (3H, s, H ), 1.29 (6H,, J 7.0 Hz, H ); δ C (CDCl 3 ) (C m ), (C ), (C j ), (C ), 86.9 (C ), 84.6 (C ), 80.9 (C ), 79.8 (C ), 35.3 (C l ), 31.7 (C ), 22.9 (C ), 22.7 (C ), 18.8 (C ); δ P (CDCl 3 ) (spt.); δ F (CDCl 3 ) (); m/z (HRMS + ) [M PF 6 ] + (C 18 H Ru rqurs ); R = 0.05 (sl, CH 2 Cl 2 : 5% EtH).

7 j l ' ' ' ' ' ' ' ' ' j' ' l' 2-[2-(Cylopnt-1,3-n-1-yl)tyl]pyrn n 2-[2-(ylopnt-1,4-n-1-yl)tyl]pyrn PP 3 (6.98, 26.6 mmol) n CBr 4 (8.82, 26.6 mmol) wr to soluton o 2-Pyrntnol (2.00 ml, 17.8 mmol) n nyrous THF (40 ml). T mxtur ws strr t 20 C or 24 or xss slts wr rmov y ltrton. T ru 2-(2-romotyl)pyrn soluton ws ool to -78 C n soluton o soum ylopntnyl (2M n THF, 8.90 ml) ws. T mxtur ws strr or 16 unr n ron tmospr, urn w tm t tmprtur nrs to 20 C. T solvnt ws rmov unr ru prssur to v l rsu, w ws trturt wt xn (15 ml) n tn Et 2 (50 ml). T orn rtons wr pss trou plu o sl, w ws ws wt urtr rtons o Et 2 (100 ml). All orn rtons wr omn n t solvnt rmov unr ru prssur to v 1 : 1 mxtur o t ttl ompouns s rown ol, w ws us wtout urtr purton (730 m, 24%); δ H (CDCl 3 ) 8.50 (2H, m, H l/l ), 7.54 (2H, m, H j/j ), 7.10 (4H, m, H / // ) (6H, m, H / // // ), 3.00 (4H, m, H / ), 2.87 (4H, m, H / ), 2.80 (4H, m, H / ); δ C (CDCl 3 ) (C / ),149.6 (C l/l ), (C j/j ), n (C / ), (C / // // ), (C / ), (C / ), 43.4 n 41.2 (C / ), 38.5 n 37.7 (C / ), 30.7 n 29.7 (C / ); m/z (HRMS + ) [M + ] + (C 12 H 13 rqurs ). Ru + PF 6 j l n - m q o p 2-(2-Cylopntnyltyl)pyrn(p-ymn)rutnum(II) xluoropospt, 5 A 1 : 1 mxtur o 2-[2-(ylopnt-1,3-n-1-yl)tyl]pyrn n 2-[2-(ylopnt-1,4-n-1- yl)tyl]pyrn (500 m, 2.92 mmol) ws ssolv n ry, ss (3 r tw yl) EtH (6 ml). 2 C 3 (184 m, 1.74 mmol) n [Ru(p-ymn)Cl 2 ] 2 (150 m, 0.25 mmol) wr n t mxtur ws strr unr ron t 75 C or 16. T mxtur ws lt to stn or t suprntnt ws nt rom rsul slts n ru n volum to 2.5 ml. An quous soluton o H 4 PF 6 (0.15 M, 11.5 ml) ws n t mxtur ws xtrt wt CH 2 Cl 2 (3 15 ml). T orn rtons wr omn, r ovr MS 4 n t solvnt ws rmov unr ru prssur to v rown ol. Purton y olumn romtorpy (sl, CH 2 Cl 2 : EtH 0 1% n 0.1% nrmnts) v t ttl ompoun s yllow ol (110 m, 40%); δ H (CDCl 3 ) 8.48, (1H,, J, 1.8 Hz, H q ), 7.60 (1H, t, J 7.5 Hz, 1.8 Hz, H o ), (2H, m, H n/p ), 6.00 (4H, m, H / ), 5.13 (4H, m, H / ), 2.94 (2H, t, J 7.2 Hz, H l ), 2.68 (2H, t, J 7.2 Hz, H ), 2.65 (1H, spt., J 7.0 Hz, H ), 2.27 (3H, s, H ), 1.21 (6H,, J 7.0 Hz, H ); δ C (CDCl 3 ) (C m ), (C q ), (C o ),

8 123.5 (C n ), (C p ), (C ), (C j ), (C ), 86.8 (C ), 84.4 (C ), 80.8 (C ), 80.1 (C ), 38.9 (C l ), 31.9 (C ), 27.3 (C ), 23.4 (C ), 19.6 (C ); δ P (CDCl 3 ) (spt.); δ F (CDCl 3 ) (); m/z (HRMS + ) [M PF 6 ] + (C 22 H Ru rqurs ); R = 0.10 (sl, CH 2 Cl 2 : 5% EtH). H 2-(Hyroxymtyl)ylox-2-n-1-on 1 Follown ltrtur prour, 1 ylox-2-n-1-on (12.0, mmol), ormly (20.3 ml, 37% quous) n 4-(mtylmno)pyrn (1.53, 2.50 mmol) wr to nyrous THF (25 ml) n t mxtur ws strr t 20 C or 16. T mxtur ws to ph 4 wt t ton o lut HCl n xtrt wt CH 2 Cl 2 (3 30 ml). T orn rtons wr omn, r ovr MS 4 n t solvnt ws rmov unr ru prssur to v yllow ol. Purton y olumn romtorpy (sl, Et 2 : 25 % CH 2 Cl 2 ) v t ttl ompoun s yllow ol (7.38, 46%); δ H (CDCl 3 ) 6.94 (1H, t, J 4.2 Hz, H ), 4.22 (2H,, J 6.0 Hz, H ), 2.90 (1H, m, H ), 2.40 (4H, m, H / ), 1.99 (2H, qun, J 6.3 Hz, H ); δ C (CDCl 3 ) (C ), (C ), (C ), 62.1 (C ), 38.3 (C ), 25.7 (C ), 22.8 (C ); m/z (HRMS + ) [M + ] + (C 7 H 10 2 rqurs ); R = 0.26 (sl, CH 2 Cl 2 : 2.5% MH). M S (6-xoylox-1-n-1-yl)mtyl mtnsulont 2-(Hyroxymtyl)ylox-2-n-1-on (310 m, 2.46 mmol) ws ssolv n nyrous THF (15 ml). Et 3 (1.03 ml, 7.39 mmol) n mtnsulonyl lor (275 μl, 3.55 mmol) wr n t mxtur ws strr t 0 C or 1. T solvnt ws rmov unr ru prssur n t yllow rsu ws ssolv n CH 2 Cl 2 (25 ml) n ws wt quous sturt Cl soluton (1 25 ml). T quous lyr ws rxtrt wt CH 2 Cl 2 (2 15 ml). T orn rtons wr omn, r ovr MS 4 n t solvnt ws rmov unr ru prssur to v t ttl ompoun s yllow ol (260 m, 52%); δ H (CDCl 3 ) 7.12 (1H, t, J 4.2 Hz, H ), 4.76 (2H, s, H ), 3.01 (3H, s, H ), 2.42 (4H, m, H / ), 1.99 (2H, qun, J 6.3 Hz, H ); δ C (CDCl 3 ) (C ), (C ), (C ), 67.1 (C ), 37.9 (C ), 37.4 (C ), 26.0 (C ), 22.5 (C ); R = 0.76 (sl, CH 2 Cl 2 : 2.5% MH). 1 Hny, S. T.; mun, D., Ttrron, 2007, 63 (6),

9 l j ' ' ' ' ' ' ' l' ' ' ' j' 2-(Cylopnt-1,3-n-1-ylmtyl)ylox-2-n-1-on n 2-(ylopnt-1,4-n-1-ylmtyl)ylox-2-n- 1-on A soluton o soum ylopntnyl (2 M n THF, 0.67 ml) ws lut n THF (2 ml) n ropws to strr soluton o (6-oxoylox-1-n-1-yl)mtyl mtnsulont (250 m, 1.23 mmol) n THF (5 ml) t -78 C. T mxtur ws strr or 3 t -78 C or t rton tmprtur ws nrs to 20 C n t mxtur ws strr or urtr 14. T solvnt ws rmov unr ru prssur to v yllow rsu. Purton y olumn romtorpy (sl, CH 2 Cl 2 ) v 1 : 1 mxtur o t ttl ompouns s yllow ol (54 m, 25%); δ H (CDCl 3 ) 6.60 (2H, m, H l/l ), (6H, m, H / // // ), 3.22 (4H, m, H / ), 2.85 (4H, m, H / ), 2.39 (4H, m, H / ), 2.29 (4H, m, H / ), 1.92 (4H, qun., J 6.3 Hz, H j/j ); δ C (CDCl 3 ) n (C / ), n (C / ), (C l/l ), (C / // // ), (C / ), 43.4 n 41.4 (C / ), 38.5 (C / ), 30.3 n 29.4 (C / ), 26.1 (C / ), 23.1 (C j/j ); m/z (HRMS + ) [M + ] + (C 12 H 14 rqurs ); R = 0.68 (sl, CH 2 Cl 2 : 2.5% CH 3 H). PF 6 Ru + m n - o j l q p 2-(Cylopntnylmtyl)ylox-2-n-1-on(p-ymn)rutnum(II) xluoropospt, 6 A 1 : 1 mxtur o 2-(ylopnt-1,3-n-1-ylmtyl)ylox-2-n-1-on n 2-(ylopnt-1,4-n-1- ylmtyl)ylox-2-n-1-on (50 m, 0.29 mmol) ws ssolv n ry, ss (3 r tw yl) EtH (5 ml). 2 C 3 (18.4 m, 0.18 mmol) n [Ru(p-ymn)Cl 2 ] 2 (15.3 m, mmol) wr n t mxtur ws strr unr ron t 75 C or 16. T rton mxtur ws ool n n quous soluton o H 4 PF 6 (0.15 M, 1.2 ml) ws. Atonl H 2 ws (3 ml) or t mxtur ws xtrt wt CH 2 Cl 2 (3 8 ml). T orn rtons wr omn, r ovr MS 4 n t solvnt ws rmov unr ru prssur to v rown ol. Purton y olumn romtorpy (sl, CH 2 Cl 2 : EtH 0 0.5% n 0.1% nrmnts) v t ttl ompoun s yllow ol (5 m, 3%); prtl δ H (CDCl 3 ) 6.88 (1H, t, J 4.2 Hz, H q ), 6.05 (4H, m, H / ), 5.25 (4H, m, H / ), 2.18 (3H, s, H ), (r m, H n/o/p ), 1.24 (6H,, J 7.0 Hz, H ); m/z (HRMS + ) [M PF 6 ] + (C 22 H Ru rqurs ); R = 0.25 (sl, CH 2 Cl 2 : 5% EtH).

10 Mss Sptromtry Clrton Ps n t mss sptrum r nrlly us or qulttv nlyss. Quntttv nlyss s ult s t sz o t p n t mss sptrum s pnnt upon not only t quntty o t ompoun ut lso t voltlty n t propnsty o t ompoun to ons. To llow n pproxmt quntton o t mount o omplx urn t xn xprmnts, t ollown lrton ws unrtn: to soluton o [CpRu(p-ymn)]PF 6 (5 m) n CDCl 3 (0.7 ml), [CpRu(C 6 M 6 )]PF 6 ws n ~2 m nrmnts. Atr ton, t rto o [CpRu(p-ymn)]PF 6 : [CpRu(C 6 M 6 )]PF 6 ws qunt usn 1 H-MR sptrosopy. A mss sptrum ws lso ror tr ton n t rto o ps n t mss sptrum ws plott s unton o t solut rto, trmn y 1 H-MR. T rsultn lrton urv (Fur S1) plott s t prnt o [CpRu(C 6 M 6 )]PF 6 ws us to pproxmt t xtnt o xn n t rn xn xprmnts sr n t ull txt (Sm S1). % [CpRu(C6M6)]PF6 (MS % [CpRu(C6M6)]PF6 (MR t) Fur S1. Clrton urv us to trmn t prnt [CpRu(C 6 M 6 )]PF 6 rom mss sptromtr t. Hl L Clulton T l-l o strtn p-ymn omplx unr t xn ontons sown (Sm S1) ws lult or our omplxs (1, 3, 5 n 6), orn to Prour S2. Dt or omplxs 1 n 5 r sown (Fur S2) n l-l vlus or omplx s vn n Tl S q. R Ru II Cyloxnon, 150 o C R Ru II Sm S1 Prour S2

11 [CpRu(p-ymn)]PF 6 (1.0 m, 2.2 μmol), xmtylnzn (36.4 m, 225 μmol) n ry, ss yloxnon or 1-otnol (1.00 ml) wr strr t 150 C n sl Sln tu. Alquots wr tn t tn slt tm ponts n t xtnt o xn ws pproxmt usn postv on mo ltrospry mss sptromtry n t lrton urv sr ov. T t wr plott s %strtn p-ymn omplx s unton o tm (Fur S2). T l-l or omplx ws lult orn to Equton S1.1 n Equton S1.2 usn lst squrs ttn n Mrosot Exl. [A] t = [A] 0 t t 1 2 = ln2 [S1.1] [S1.2] [A] = onntrton o strtn p-ymn omplx; [A] 0 = ntl onntrton o strtn p-ymn omplx; = rt onstnt or xn; t = tm; n t 1/2 s t l-l o t strtn omplx. % Strtn Complx Tm / Fur S2: Prnt o rn xn n t pross sown n Sm S1 t tn tm ponts or omplxs 1 n 5. Tl S5. Hl-lvs or omplxs 1, 3, 5 n 6 lult or t xn pross sown n Sm S1, (ontons: yloxnon, 150 C, 100 quvlnts o nomn rn). Complx Hl L ± ± ± ± 0.4

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