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. 2025 Mar 4;21:490–499. doi: 10.3762/bjoc.21.36

Table 3.

Vinylation of halogenated N-acetyl diazocines via Pd-catalyzed coupling reactions. Equivalents are normalized to the used amount of N-acetyl diazocine starting material.

graphic file with name Beilstein_J_Org_Chem-21-490-i002.jpg
cat. system reaction partner or additive conditions yield
Pd(OAc)2 (0.1 equiv) + PPh3 (0.8 equiv) tributylvinyltin (1 equiv) dry DMF, N2, 100 °C, 16 h X = Br, 65%
X = I, 71%
PdBr2 (0.1 equiv) + JohnPhos (0.1 equiv) D4Va (0.66 equiv)
TBAF (4 equiv)		 dry THF, N2, 50° C, 16 h X = Br, 74%
X = I, 78%

aD4V: 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane.