The dearomative [5 + 1] annulation of 2-methylindoles with new five-membered synthon was developed through cascade [1,5]-hydride transfer/dearomative cyclization in HFIP for the synthesis of spirochromanes bearing the 2-methylindolenine skeleton.

This review highlights the encouraging advances in hydride transfer-involved dearomatization reaction during the past decade, the content of which is categorized according to the hydride acceptors, namely vinylogous imines and quinone methides.

The use of alkyl amines and ethers as traceless hydride donors in [1,5]-hydride transfer cascade reactions has been reviewed herein.