Journal of the American Chemical Society p. 7219 - 7225 (1993)
Update date:2022-07-30
Topics:
Ishiyama, Tatsuo
Nishijima, Koh-Ichi
Miyaura, Norio
Suzuki, Akira
Theaddition of 9-(alkylthio)-9-borabicyclo[3.3.1]nonanes(9-(RS)-9-BBN) 1 to terminal alkynes was catalyzed by Pd(PPh3)4 (3 mol %) to produce 9-[(Z)-2-(alkylthio)-1-alkenyl]-9-BBN derivatives 2 in high yields. The reactions were highly regio- and stereoselective, and their conditions were sufficiently mild that a variety of functionalized alkenylboranes 2 with defined stereochemistry were readily synthesized. The boranes 2 exhibited exceptionally high reactivity on protonolysis with methanol to produce the Markovnikov adducts of thiols to 1-alkynes, 2-(alkylthio)-1-alkenes 3. The synthetic utility of the present reaction was demonstrated by the regio- and stereoselective one-pot synthesis of alkenyl sulfides 7 via the palladium-catalyzed thioboration-cross-coupling sequence.
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