"Front Matter". In: Organosilanes in Radical Chemistry - Index of

Tris(trimethylsilyl)silane 63
86% yield (Reaction 4.32), whereas other radical-based reducing systems give
much poorer yields [69].
PhOC(S)O
(TMS) 3 SiH
AIBN, 80 �C
94%
O
O
O
O
O
(TMS) 3SiH O
O O
O
O
Et3B, O2 , r.t.
O
O
S
C6H4-p-F 94%
O
P(OMe) 2 (TMS) 3SiH CH-OC(S)OPh
CH
AIBN, 80 �C
2
CH-C(O)OBu-t
NHBoc
O
OH
PhOC(S)O OC(S)OPh
O
P(OMe) 2
TFA
CH2 CH2 CH-C(O)OBu-t
NHBoc
(TMS) 3SiH
AIBN, 80 �C
O
P(OMe) 2
CH2 CH2 CH-C(O)OBu-t
NH +
3 CF3CO2− 72% (2 steps)
O
OH
86%
(4.29)
(4.30)
(4.31)
(4.32)
Radical deoxygenation via thioimidazolyloxy derivatives is also found to be
efficient process. Two examples are reported in Reactions (4.33) and (4.34)
[70,71]. In particular, dideoxygenation was useful to prove the structure of the
stemodane ring system, achieved by other routes.
BnO
N
O
N
O
S
O
O
(TMS) 3SiH AIBN, 80 �C
BnO
O
92%
O
O
(4.33)