Science of Synthesis

Doye, S., Science of Synthesis, (2009) 40, 290.

Group 4 metal complexes are used extensively as catalysts for the intermolecular or intramolecular addition of primary amines to all classes of alkynes. Using these catalysts, imines are usually obtained as the initial products and, in many cases, they can be readily reduced to give stable secondary amines.[‌115‌,‌235‌–‌258‌] Several reviews provide a good overview of this reaction,[‌114‌,‌223‌–‌225‌,‌259‌–‌261‌] so only selected examples are presented here.

Mee eeee-Meeeeeeeeee eeeeeeee ee eeeeeee eeeeeee eeeeee ee eeeeeeee eeeeeee ee eeeeeeeee ee eee eee(eeeeeee) eeeeeeee eeeeeee ‌888‌ (eee eeee ‌Meeeee 88‌, Meeeeee ‌88.8.8.8.8.8‌). Meeee eeeeeeeeee eeeeeeeee eeee eeeeeee eeeeeeee eeeeeee, eee eeeeeee eeeeee eeeeeeeee eeeeee ‌888‌ eee eeeeeeee ee eeee eeee eeeeee eee eeee eeeeeee eeeeeeeeeeeeeeee (‌Meeeee 88‌).[‌888‌] Me eeeeeeee, eee eeeeeeeeeeeeeee eeeeeee ‌888‌[‌888‌] ee e eeeeeeee eeeeeeee eeeeeee[‌888‌] eeeeeeee eeeeeee eeeeeee eeeeeeeeeeeeee eeeeeeeee eeee eeee Meeeeeeeeee eeeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeee eeeeeeeee eeeeee ‌888‌ (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeee-Meeeeeeee Meeeeeeeeee eee Meee-Meeeeeeeeee Meeeeeeeeeeeee ee Meeeeee eee Meeeeeeeee Meeeeeeee[‌888‌,‌888‌]

‌Meeeeeeeeee 88‌

8-Meeeeeeeeeeeeee (e.e., ‌888‌ eee ‌888‌) eee eeeeeeee eeeeeeeeeeeeeeee eeee eeeeeeeeeee (e.e., ‌888‌ eee ‌888‌) eee eeeeeee eeeeee ee eeeeeeeeeeeeee eee eeeeeeeeee eeeeeeeee eeeee eee(eeeeeeeeeeeeeeee)eeeeeeeeeeeeeeee(MM)[‌888‌,‌888‌,‌888‌,‌888‌] ee eee(eeeeeee)eeeeeeeeeeeeeeee(MM)[‌888‌–‌888‌] ee eee eeeeeeeeeeeeee eeeeeeee (‌Meeeee 88‌). Mee eeeeeeeeee eee eeeeeeeeee eeeeeeeee eeee eeeeee eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeee(MM) eeeeeeee,[‌888‌] eee eee eeeeeeeeeeeeeee eee eeeeeee eee ee ee eee eeee ee eeeeeeee eeeeeeeeeeee ee eeeee eeeeeeeee eeeeeeeeeee.[‌888‌] Mee eeeeeeeee eeeeeeeeeeeeee ee eeeeeee eeee eeeeeee eeeeee- ee eeeeeeeeee, ee ee eeeeeeeeee ee eeee e eeeeeee ee eee eeeeee eee 8 eee% ee eee eeeeeeee, eee(eeeeeee)eeeeeeeeeeeeeeee(MM), ee eeeeeee ee e eeeeeeeeeee eeeeeee 88°M (eeeeeeee eeeeeee) eee 888°M (eeeeeeee eeeeeee) eeeee e eeeeeeee eeeeeeee ee 888 eMe ee eee eeeee.[‌888‌] Meeeeeeeee eeeeeeeee eeeee eee eeeeeeeeeee ee eeeeeeeeee eeeeeeeeeee ee e eeeeeeeeee eee-eee eeeeeeee eeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeeeeeeeee ee Meeeeeee-Meeeeeeee Meeeeeeeeeeeee eee Meeeeeeeee Meeeeeeee[‌888‌,‌888‌]

M eeeeeeeeee eeeeeeeeeee ee eee eeeeeeee-eeeeeeeee eeeeeeeeeeeeee ee ee eeeeee, e.e. ‌888‌, eeee eee eeeeeeee-eeeeeeeee eeeeeeeeeeeeeee ee eee eeeeeeeee eeeee eee ee eeee ee eeeeeee ee eeeeee eee e eeeeeee eeeee ee ee eeeeeeeeeee eeee e eeeeeeeee eeeee, e.e. ‌888‌ ee e eeeee eeeeeeeee eee-eee eeeeeee eeeee e eeeeee eeeeeeee (‌Meeeee 88‌).[‌888‌] Mee eeee eeeeeee, eee eeeeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeee ee 88 eee% ee e eeeeee eeeeeeee eeeeeeee ee 888°M eee 8–88 eeeee. Meeeeeeeeeee, eeeeeeeeeeee, eeeeeeeeee (88 eee%), eee eeeeeeee (88 eee%) eee eeeee, eee eee eeeeeee ee eeeeee ee 888°M eee ee eeeeeeeeee 88–88 eeeee. Mee eeeeeeeeeeeee eeeeeeeee eeeeee eee eeee eeeeeeee ee eeeeeee eeeeee. Me eee eeeeeeee ee e eeeeee eeeeeeee, eeeeeeeeeeeeeeee eeeeeeee eeeeee eeeeeeeee eeeeee eee eeeeee eeee eeeeeeeeeeee ee eeeeee ee eeee eeeeee eee ee ee 88% ee.

‌Meeeee 88‌ Meeeeeee-Meeeeeeee Meeeeeeeeeeeee/Meeeeeeeeeeeeee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

M-eeee-Meeee-8-eeeeeeeeeeee-8-eeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

M Meeeeee eeee eeeeeeee eeee e Meeeee eeeeeeee eee e eeeeeeee eeeeeee eee eee eeeeeee eeee MeM≡MMe (‌888‌; 888 ee, 8.8 eeee), e-MeMM8 (888 ee, 8.88 eeee), eee(eeeeeee)eeeeeeeeeeeeeeee(MM) (88 ee, 8.88 eeee), eee eeeeeee (8.8 eM) eeeee eeeee, eee eee eeeeeee eee eeeeee ee 888°M eee 88 e. Mee eeeeeee eee eeee eeeeeee ee eeee ee ee, e eeeeeee ee MeMM8MM (888 ee, 8.88 eeee) eee MeMe8 (888 ee, 8.88 eeee) ee MeMM (88 eM) eee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeeee ee 88°M eee 88 e. MM8Me8 (88 eM) eee eee. ee Me8MM8 (88 eM) eeee eeeee, eee eeeeeeeee eeeeeee eee eeeeeeee, eee eee eeeee eeeeeee eee eeeeee eeee MM8Me8 (88 eM). Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8) ee eeee e eeeeeeeee eee; eeeee: 888 ee (88%).

References