Palladium(0)-Catalysed Stannylstannylation and Silylstannylation of 1-Alkoxy-1-alkynes and 1-Phenylthio-1-alkynes

Sharon Casson; Philip Kocienski; Gillian Reid; Nicholas Smith; Joan M. Street; Michael Webster

doi:10.1055/s-1994-25685

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Synthesis 1994; 1994(12): 1301-1309
DOI: 10.1055/s-1994-25685

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Palladium(0)-Catalysed Stannylstannylation and Silylstannylation of 1-Alkoxy-1-alkynes and 1-Phenylthio-1-alkynes

Sharon Casson^* , Philip Kocienski, Gillian Reid, Nicholas Smith, Joan M. Street, Michael Webster

^*Chemistry Department, The University, Southampton, SO17 1BJ, U.K.

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Publication Date:
25 April 2002 (online)

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1-Alkoxy-1-alkynes and 1-phenylthio-1-alkynes add Me₃Si-SnMe₃ in the presence of catalytic amounts of Pd(0) . Clean syn-addition is observed with the Me₃Sn group being placed exclusively α to the heteroatom. The regio- and stereochemistry was confirmed by NMR spectroscopy and X-ray analysis. 1-Alkoxy-1-alkynes also add Me₃Sn-SnMe₃ under similar conditions.