Transition Metal Free Chemoselective Reduction of α,β‐Unsaturated Ketones to Saturated Ketones Using Tosyl Hydrazide as a Hydrogen Donor

Abstract

An efficient, inexpensive and simple method for the reduction of various α,β-unsaturated ketones to corresponding saturated ketones using tosyl hydrazide as a hydrogen donor in DMF using calcium oxide powder has been reported. A variety of enones underwent reduction without forming undesirable side products. High chemoselectivity, broad functional group tolerance and good yields are the noteworthy features of this protocol.

Efficient Organoruthenium Catalysts for α‐Alkylation of Ketones and Amide with Alcohols: Synthesis of Quinolines via Hydrogen Borrowing Strategy and their Mechanistic Studies

“…3‐(3,4‐dimethoxyphenyl)‐1‐(4‐methoxyphenyl)propan‐1‐one (3 dc) Yield 276.3 mg 92 % (Catalyst Ru1 ), 279.3 mg 93 % (Catalyst Ru2 ); 1 H NMR (400 MHz, CDCl 3 ) δ 7.92 (d, J =9.0 Hz, 2H), 6.90 (d, J =8.9 Hz, 2H), .76 (q, J =4.5, 1.9 Hz, 3H), 3.84 (s, 3H), 3.83 (s, 3H), 3.83 (s, 3H), 3.20 (t, J =7.6 Hz, 2H), 2.98 (t, J =7.7 Hz, 2H). 13 C NMR (101 MHz, CDCl 3 ) δ 198.05, 163.52, 148.95, 147.43, 134.16, 130.38, 130.05, 120.25, 113.80, 111.91, 111.41, 100.00, 55.90, 40.40, 30.08.…”

Frustrated Lewis pairs in two-dimensional borocarbonitride for the facile synthesis of 3-aminoimidazo[1,2-α]pyridines using TMSCN as an isonitrile substitute

“…The synthesis of imidazo[1,2-a]pyridines from alcohols using a DMSO-propylphosphonic anhydride (T3P s ) medium as an oxidizing and cyclodehydrating agent has been reported, 22 but the main drawback of this protocol is the high cost of T3P s and the use of isocyanides. 23,24 Among metal-free catalysts, [25][26][27][28][29] boron (B)-based nonmetallic catalysts have attracted much attention in present research for various applications. [30][31][32][33][34][35][36] However, as an electron-deficient Lewis acid catalyst, the empty sp 2 orbital of boron can interact with the lone pair of electrons of nitrogen, which suppresses the catalytic activity of BCN.…”

“…Among metal-free catalysts, 25–29 boron (B)-based nonmetallic catalysts have attracted much attention in present research for various applications. 30–36 However, as an electron-deficient Lewis acid catalyst, the empty sp 2 orbital of boron can interact with the lone pair of electrons of nitrogen, which suppresses the catalytic activity of BCN.…”