Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409, USA.
Department of Chemistry and Biochemistry, University of California Merced, Merced, California 95343, USA.
Org Biomol Chem. 2022 May 11;20(18):3675-3702. doi: 10.1039/d2ob00162d.
The catalytic hydroboration of imines, nitriles, and carbodiimides is a powerful method of preparing amines which are key synthetic intermediates in the synthesis of many value-added products. Imine hydroboration has perennially featured in notable reports while nitrile and carbodiimide hydroboration have gained attention recently. Initial developments in catalytic hydroboration of imines and nitriles employed precious metals and typically required harsh reaction conditions. More recent advances have shifted toward the use of base metal and main group element catalysis and milder reaction conditions. In this survey, we review metal and nonmetal catalyzed hydroboration of these unsaturated organic molecules and group them into three distinct categories: precious metals, base metals, and main group catalysts. The TON and TOF of imine hydroboration catalysts are reported and summarized with a brief overview of recent advances in the field. Mechanistic and kinetic studies of some of these protocols are also presented.
亚胺、腈和碳二亚胺的催化氢化硼化是一种制备胺的有效方法，胺是许多增值产品合成中的关键合成中间体。亚胺氢化硼化一直是重要报道的主题，而腈和碳二亚胺氢化硼化最近也受到了关注。亚胺和腈的催化氢化硼化的最初发展采用了贵金属，并且通常需要苛刻的反应条件。最近的进展已经转向使用基础金属和主族元素催化以及更温和的反应条件。在本综述中，我们综述了这些不饱和有机分子的金属和非金属催化氢化硼化，并将它们分为三类：贵金属、基础金属和主族催化剂。报道了亚胺氢化硼化催化剂的TON 和 TOF，并简要概述了该领域的最新进展。还介绍了这些方案中的一些机理和动力学研究。
