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. Author manuscript; available in PMC: 2011 Dec 22.
Published in final edited form as: J Am Chem Soc. 2010 Nov 29;132(50):17933–17944. doi: 10.1021/ja1086485

Table 9.

Nucleophilic additions to 6,7-indolynes with varying N-substituentsa

graphic file with name nihms255340u6.jpg
trapping agent (Nuc) N-substitudent (R) yield ratio (C6 : C7)
graphic file with name nihms255340t33.jpg Me 53% C6 only
H 52% 10.7 : 1
Boc 59% C6 only
graphic file with name nihms255340t34.jpg Me 91% C6 only
H 79% 13.8 : 1
Boc 66% C6 only
Bn–N3 Me 77% C6 only
H 60% 6.9 : 1
Boc 63% C6 only
KCN Me 70% C6 only
H 44% 7.6 : 1
Boc 80% C6 only
a

Conditions: see supporting information.