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. Author manuscript; available in PMC: 2017 Nov 9.
Published in final edited form as: J Am Chem Soc. 2016 Oct 28;138(44):14570–14573. doi: 10.1021/jacs.6b09939

Table 2.

Intermolecular Multicomponent Carboamination of Alkynes and Alkenes with PhNNPha

graphic file with name nihms868680u2.jpg

Alkene R2 % Isolated Yield (6:7)b 1H NMR % Yield (6:7)c
5a graphic file with name nihms868680t14.jpg Me 54 (40:60) n.d.
5b graphic file with name nihms868680t15.jpg Et 61 (>99:1) n.d.
5c graphic file with name nihms868680t16.jpg Me 42 (9:91) 63 (15:85)d
5d graphic file with name nihms868680t17.jpg Et 51 (>99:1) 70 (71:29)e
5ef graphic file with name nihms868680t18.jpg Et 40 (>99:1) n.d.
5f graphic file with name nihms868680t19.jpg Et 0 n.d.
a

Loading of [py2TiCl2NPh]2 and reaction yields with respect to PhNNPh.

b

Isolated as the ketone product after hydrolysis. See SI for details.

c

Determined by 1H NMR analysis of the crude reaction mixture.

d

96:4 ratio of cis:trans cyclopropane product.

e

74:26 ratio of cis:trans cyclopropane product.

f

Reaction run in neat alkene.