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1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry Supporting Information General Remarks Most of chemicals were purchased from Sigma-Aldrich, Strem, Acros, TCI or Alfa, used as such unless stated otherwise and methyl benzylcarbamate was synthesized. Solvents (Anhydrous and under inert atmosphere) were collected from The Solvent purification system by M BRAUN and used under standard schlenk technique. NMR spectra were recorded on Bruker Avance and Bruker ARX spectrometers. Chemical shifts (ppm) are given relative to solvent: references for CDCl were. ppm ( H NMR) and. ppm ( C NMR). Multiplets were assigned as s (singlet), d (doublet), t (triplet), q (quartet), p (pentet) dd (doublet of doublet), m (multiplet) and br. s (broad singlet). GC-yields were calculated using isooctane as internal standard. All measurements were carried out at room temperature unless otherwise stated. Electron impact (EI) mass spectra were recorded on AMD mass spectrometer ( ev). High resolution mass spectra (HRMS) were recorded on Agilent. The data are given as mass units per charge (m/z). Gas chromatography analysis was performed on an Agilent HP-A instrument with a ID detector and HP- capillary column (polydimethylsiloxane with % phenyl groups, m,. mm i.d.,. μm film thickness) using argon as carrier gas. The products were isolated from the reaction mixture by column chromatography on silica gel,.-. mm, - mesh (Merck). General Procedure A ml screw-cap vial was charged with Pd(TA) (. mg, mol%), DPPP (. mg, mol%), DMC/MeH (./. ml) and an oven-dried stirring bar. The vial was closed by Teflon septum and phenolic cap and connected with atmosphere with a needle. After benzyl alcohol (. mmol) were injected by syringe, the vial was fixed in an alloy plate and put into Paar series autoclave ( ml) under argon atmosphere. At room temperature, the autoclave is flushed with carbon monoxide for three times and bar of carbon monoxide was charged. The autoclave was placed on a heating plate equipped with magnetic stirring and an aluminum block. The reaction is allowed to be heated under o C for hours. Afterwards, the autoclave is cooled to room temperature and the pressure was carefully released. After removal of solvent under reduced pressure, pure product was obtained by column chromatography on silica gel (eluent: pentane/ethyl acetate = :).
2 Analytic Data of Products Methyl -phenylacetate H NMR ( MHz, Chloroform-d) δ.. (m, H),. (s, H),. (s, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.. Methyl -(o-tolyl)acetate H NMR ( MHz, Chloroform-d) δ. (t, J =. Hz, H),. (s, H),. (s, H),. (s, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.. Methyl -(-methoxyphenyl)acetate H NMR ( MHz, Chloroform-d) δ.. (m, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.. Methyl -(-methoxyphenyl)acetate H NMR ( MHz, Chloroform-d) δ.. (m, H),. (dd, J =.,. Hz, H),.. (m, H),. (s, H),. (s, H),. (s, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.. Methyl -(naphthalen--yl)acetate H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),.. (m, H),.. (m, H),. (s, H),. (s, H).
3 C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.. Methyl -(-benzylphenyl)acetate H NMR ( MHz, Chloroform-d) δ.. (m, H),. (s, H),. (d, J =. Hz, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.. Methyl -(-(trifluoromethyl)phenyl)acetate C H NMR ( MHz, Chloroform-d) δ.. (m, H),. (s, H),. (s, H). C NMR ( MHz, Chloroform-d) δ.,.,.. (m),. (d, J =. Hz),.,.. (m),. (q, J =. Hz),.,.. Methyl -(-((-methoxyphenyl)dimethylsilyl)phenyl)acetate Si H NMR ( MHz, Chloroform-d) δ. (ddd, J =.,.,. Hz, H),.. (m, H),.. (m, H),. (dt, J =.,. Hz, H),. (ddd, J =.,.,. Hz, H),. (ddd, J =.,.,. Hz, H),. (s, H),. (s, H),. (s, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.. Methyl -(-(trifluoromethyl)phenyl)acetate C
4 H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),.. (m, H),. (p, J =. Hz, H),. (s, H). C NMR ( MHz, Chloroform-d) δ.,.,. (d, J =. Hz),. (d, J =. Hz),.,. (q, J =. Hz),.,.,. (d, J =. Hz). Methyl -(-methoxyphenyl)acetate H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),. (s, H),. (s, H),. (s, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.. Methyl -(-((trifluoromethyl)thio)phenyl)acetate C S H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),. (s, H),. (s, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.. Methyl -(-fluorophenyl)acetate H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),. (s, H),. (d, J =. Hz, H). C NMR ( MHz, Chloroform-d) δ.,. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),.,. Methyl -(benzo[d][,]dioxol--yl)acetate H NMR ( MHz, Chloroform-d) δ.. (m, H),. (s, H),. (s, H),. (t, J =. Hz, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,..
5 -(Thiophen--yl)ethyl -phenylacetate S H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),. (t, J =. Hz, H),. (s, H),.. (m, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,.,.,.,.,.. Ethyl -phenylacetate H NMR ( MHz, Chloroform-d) δ.. (m, H),. (q, J =. Hz, H),. (s, H),. (t, J =. Hz, H). C NMR ( MHz, CDCl ) δ.,.,.,.,.,.,.,..
6 .f..fid Yahui Li L- PRTN CDCl {C:\Bruker\TopSpin.pl}... -.f..fid Yahui Li L- CCPD CDCl {C:\Bruker\TopSpin.pl}
7 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.PL}.....f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.PL}
8 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.PL} f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.PL}
9 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.PL} f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.PL}
10 ...fid Yahui Li L-- AuH CDCl /opt/topspin fid Yahui Li L-- AuC CDCl /opt/topspin
11 ...fid Yahui Li L-- AuH CDCl /opt/topspin fid Yahui Li L-- AuC CDCl /opt/topspin
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13 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.pl} Si H C f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.pl} Si H C -
14 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.pl} f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.pl}
15 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.pl} f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.pl}
16 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.pl} S f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.pl} S - - -
17 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.pl} f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.pl}
18
19 .f..fid Li/ L-- PRTN CDCl {C:\Bruker\TopSpin.pl} S f..fid Li/ L-- CCPD CDCl {C:\Bruker\TopSpin.pl} S - -
20 .f..fid Yahui Li L-- PRTN CDCl {C:\Bruker\TopSpin.pl} f..fid Yahui Li L-- CCPD CDCl {C:\Bruker\TopSpin.pl}
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