A formal 1,6-conjugated addition-mediated [4 + 1] annulation of ortho-hydroxyphenyl-substituted para-quinone methides with sulfonium or ammonium bromides has been described. This domino-type process offered an efficient method for the synthesis of 2,3-dihydrobenzofurans in good yields, exhibiting good functional group tolerance, scalability and high diastereoselectivity.
A [4 + 1] annulation between newly designed ortho-electrophile-substituted para-quinone methides and nucleophiles through tandem 1,6-conjugated addition/1,4-Michael addition under mild reaction conditions has been described. This reaction provides an efficient method to construct indanes and isoindolines in moderate to good yields and with good functional group tolerance.