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. Author manuscript; available in PMC: 2021 Jul 8.
Published in final edited form as: J Am Chem Soc. 2020 Jun 24;142(27):11674–11679. doi: 10.1021/jacs.0c04533

Table 1.

Optimization of donor/donor Si–H insertion

graphic file with name nihms-1653382-t0001.jpg
entry R Rh2L4 % yielda drb erc
1 H Rh2(OAc)4 34 - 50:50
2 H Rh2(5R-MEPY]4 <5 - ND
3 H Rh2(S-BTPCP)4 <5 - ND
4 H Rh2(S-DOSP)4 65 - 55:45
5 H Rh2(R-PTAD)4 67 - 61:39
6 H Rh2(S-PTTL)4 62 - 64:36
7 H Rh2(S-BPTTL)4 62 - 64:36
8 H Rh2(S-PTV)4 67 - 59:41
9 H Rh2(S-TCPTTL)4 76 - 76:24
10 H Rh2(S-TCPTTL)4d 78 - 82:18
11 CH3 Rh2(OAc)4 45 55:45 50:50
12 CH3 Rh2(R-PTAD)4 72 60:40 ND
13 CH3 Rh2(S-DOSP)4 75 61:39 ND
14 CH3 Rh2(S-TCPTTL)4d 91 93:7 93:7
15e CH3 Rh2(S-TCPTTL)4d 81 93:7 93:7
a

NMR yield using Ph-TMS as an internal standard.

b

Determined using 1H NMR Spectroscopy.

c

Determined using CSP-HPLC analysis of silanol obtained from Pd/C hydrolysis; major diastereomer if relevant.

d

Toluene used as a solvent.

e

Diazo added via syringe over five minutes.