Ynones merge activation/conjugate addition of chalcogenoborates ArE-Bpin (E=Se, S)

author can archive pre-print (ie pre-refereeing) DOI: 10.1002/adsc.201500650 URL: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500650/abstract;jsessionid=BDAFCF7CB20C8EAEB9EE626EFD8A7F6C.f04t01 Filiació URV: SI
The ¿pull push¿ effect of the Bpin moiety in ArE-Bpin reagents (E=Se, S) is demonstrated by the Lewis acid interaction with the carbonyl group of ynones and the concomitant delivery of ArSe or ArS to the electron deficient alkyne with impressive stereoselectivity. The two component reactivity is carried out in MeOH to generate (Z)-¿-(arylseleno)-¿,¿-unsaturated ketones and (Z)-¿-(arylsulfuro)-¿,¿-unsaturated ketones with a consensus between experimental and theoretical understanding of the mechanism