4.05 Addition of H[sbnd]X Reagents to Alkenes, Alkynes, and Allenes without Transition Metal

Abstract

Heteroatom-containing compounds widely exist in nature, and are often very useful as building blocks in organic synthesis. From the atom economy point of view, the direct formation of a new CX bond by addition of HX to an unsaturated CC bond is of particular significance. A number of procedures have been developed that offer important advantages in chemo-, regio-, or stereoselectivity. This chapter reviews the most representative reports from 1990 to 2012 on the addition of the elements HX (where Xhalogen, nitrogen, oxygen, sulfur, phosphorus, and selenium) to alkenes, alkynes, and allenes. In this chapter, metal-mediated addition of HX to CC multiple bonds will not be covered, except a few examples of mercury- and gold-mediated reactions and hetero-Michael reaction (Xnitrogen, oxygen, sulfur, etc.) of electron-deficient alkenes, alkynes, and allenes in order to avoid the overlap with related chapters in this volume.