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. Author manuscript; available in PMC: 2012 Aug 24.
Published in final edited form as: J Am Chem Soc. 2011 Aug 1;133(33):13002–13005. doi: 10.1021/ja2057852

Table 1.

Directed heterodimer synthesis.

Entry Unsymmetrical Sulfamidea Diazeneb Heterodimeric Productc
1 graphic file with name nihms314815t1.jpg 5d, (80) graphic file with name nihms314815t2.jpg
2 graphic file with name nihms314815t3.jpg 5e, (88) graphic file with name nihms314815t4.jpg
3 graphic file with name nihms314815t5.jpg 5f, (83) graphic file with name nihms314815t6.jpg
4 graphic file with name nihms314815t7.jpg 5g, (99) graphic file with name nihms314815t8.jpg
5 graphic file with name nihms314815t9.jpg 5h, (91)d graphic file with name nihms314815t10.jpg
6 R = CF3, 6i, 57 5i, (99) (+)-4i, 61 [60% 2-steps]
a

Mixed sulfamide synthesis: 7, 13, DMAP, Et3N, CH2Cl2, 0 → 23 °C. Isolated % yield of 6 after chromatography.

b

Diazene synthesis: BEMP, NCS, THF, 23 °C. Crude % yield of sensitive diazene 5 in parentheses.

c

Heterodimer synthesis: t-BuOH, hν >280 nm, 23 °C, 5 h. Isolated % yield of 4 after chromatography. Yield of 4 from 6 in brackets.

d

DBU, NCS, MeOH, 0 → 23 °C.

e

hν 300 nm, 12 h.