Construction of fully substituted carbon centers containing a heteroatom and a CF3 group via in situ generated p-quinone methides

1,6-Conjugate additions of in situ generated delta-CF3-delta-substituted p-quinone methides have been achieved with a variety of heteronucleophiles under mild conditions, which led to facile and practical construction of fully substituted carbon centers including a heteroatom and a CF3 group. In particular, it was revealed that some amines themselves worked for efficient cleavage of the TBS protective group, and addition of a catalytic amount of an appropriate Bronsted acid was found to sometimes improve the progress of the desired process.

Automated summary

The 1,6-conjugate additions of in situ generated delta-CF3-delta-substituted p-quinone methides with various heteronucleophiles under mild conditions successfully led to the construction of fully substituted carbon centers, including a heteroatom and a CF3 group. It was also discovered that some amines can efficiently cleave the TBS protective group, and the addition of a catalytic amount of an appropriate Bronsted acid can enhance the progress of the desired process.