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. Author manuscript; available in PMC: 2011 Sep 2.
Published in final edited form as: J Am Chem Soc. 2009 Feb 18;131(6):2066–2067. doi: 10.1021/ja809456u

Table 3.

Ruthenium catalyzed transfer hydrogenative coupling of alkynes 6a–6c to aldehyde 4b (top) and alcohol 1b (bottom).a

graphic file with name nihms91403u4.jpg
Entry Alkyne (200 mol%) Product Time (hr) Yield (2:3)
1 6a, R1 = Ph 2m (3m) 24 hr 91% (>20:1)
2 6b, R1 = (CH2)2OBn 2n (3n) 16 hr 84% (>20:1)
3 6c, R1 = CH2NHBoc 2o (3o) 13 hr 75% (>20:1)
graphic file with name nihms91403u5.jpg
Entry Alkyne (200 mol%) Product Time (hr) Yield 2 (3)
1 6a, R1 = Ph 2m (3m) 37 hr 62% (12%)
2 6b, R1 = (CH2)2OBn 2n (3n) 13 hr 58% (>1%)
3 6c, R1 = CH2NHBoc 2o (3o) 13 hr 15% (>1%)
a

See supporting information for detailed procedures. Isolated yields refer to pure 2m–2o free of any enone byproduct.