SUPPORTING INFORMATION FOR

A Direct Route from White Phosphorus and Fluorous Alkyl and Aryl Iodides to the

Corresponding Trialkyl- and Triarylphosphines

Subrata K. Ghosh,a Christopher C. Cummins,*b and John A. Gladysz*a

aDepartment of Chemistry, Texas A&M University, PO Box 30012, College Station, Texas

77843-3012, USA

E-mail: gladysz@mail.chem.tamu.edu

bDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue,

Cambridge, Massachusetts 02139-4307, USA

E-mail: ccummins@mit.edu

Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.This journal is © the Partner Organisations 2018

-s2-

P((CH2)2Rf8)31H NMR (CF3C6F11, 500 MHz), internal C6D6 filled capillary

13C{1H} NMR (CF3C6F11, 125 MHz), internal C6D6 filled capillary

-s3-

31P{1H} NMR (CF3C6F11, 202 MHz), 85% aqueous H3PO4 external standard

-600-550-500-450-400-350-300-250-200-150-100-50050100150200250300350400f1 (ppm)

-25.

20

-s4-

P((CH2)2Rf10)31H NMR (CF3C6F11, 500 MHz), internal C6D6 filled capillary

13C{1H} NMR (CF3C6F11, 125 MHz), internal C6D6 filled capillary

-s5-

31P{1H} NMR (CF3C6F11, 202 MHz), 85% aqueous H3PO4 external standard

-260-220-180-140-100-80-60-40-20020406080100120140160180200220240260280f1 (ppm)

-25.

95

-s6-

P((CH2)3Rf6)31H NMR (CDCl3, 500 MHz)

13C{1H} NMR (CDCl3, 125 MHz)

-s7-

31P{1H} NMR (CDCl3, 202 MHz), 85% aqueous H3PO4 external standard

-600-550-500-450-400-350-300-250-200-150-100-50050100150200250300350400f1 (ppm)

-33.

16

-s8-

P((CH2)3Rf8)31H NMR (CF3C6F11, 500 MHz), internal C6D6 filled capillary

13C{1H} NMR (CF3C6F11, 125 MHz), internal C6D6 filled capillary

-s9-

31P{1H} NMR (CF3C6F11, 202 MHz), 85% aqueous H3PO4 external standard

-600-550-500-450-400-350-300-250-200-150-100-50050100150200250300350f1 (ppm)

-33.

52

-s10-

P((CH2)4Rf8)31H NMR (CF3C6F11, 500 MHz), internal C6D6 filled capillary

13C{1H} NMR (CF3C6F11, 125 MHz), internal C6D6 filled capillary

-s11-

31P{1H} NMR (CF3C6F11, 202 MHz), 85% aqueous H3PO4 external standard

-600-550-500-450-400-350-300-250-200-150-100-50050100150200250300350400f1 (ppm)

-32.

07

-s12-

P(C6H3(3,5-Rf6)2)31H NMR (FC-72, 500 MHz), internal C6D6 filled capillary

31P{1H} NMR (FC-72, 202 MHz), 85% aqueous H3PO4 external standard

-180-160-140-120-100-80-60-40-20020406080100120140160180f1 (ppm)

-5.3

4

-s13-

P(C6H4(3-Rf6))31H NMR (CDCl3, 500 MHz)

31P{1H} NMR (CDCl3, 202 MHz), 85% aqueous H3PO4 external standard

-180-160-140-120-100-80-60-40-20020406080100120140160180f1 (ppm)

-6.3

4

-s14-

P(C6H4(4-Rf6))31H NMR (acetone-d6, 500 MHz)

31P{1H} NMR (acetone-d6, 202 MHz), 85% aqueous H3PO4 external standard

-180-160-140-120-100-80-60-40-20020406080100120140160180f1 (ppm)

-6.3

3