Harvard College

Theodore Alexander Betley

Elisabeth Therese Hennessy

Roy Gerald Gordon

Alan Aspuru-Guzik

Michael J Aziz

Michael S Marshak

Brian Huskinson

Suleyman Er

Changwon Suh

Yuyang Dong

Yunjung Baek

Alexandre Mikhailine

Claudia Kleinlein

Disclosed are compounds, methods, reagents, systems, and kits for the preparation and utilization of monomeric or polymeric metal-based compounds. These metal-based compounds are organometallic catalysts composed of substituted dipyrrin ligands bound to transition metals. C—H bond functionalization catalysis can be performed with the disclosed organometallic catalysts to yield C—N bonds to generate substituted bicyclic, spiro, and fused nitrogen-containing heterocycles, all common motifs in various pharmaceutical and bioactive molecules.

Annulation catalysts via direct C—H bond amination

The invention provides an electrochemical cell based on a new chemistry for a flow battery for large scale, e.g., gridscale, electrical energy storage. Electrical energy is stored chemically at an electrochemical electrode by the protonation of small organic molecules called quinones to hydroquinones. The proton is provided by a complementary electrochemical reaction at the other electrode. These reactions are reversed to deliver electrical energy. A flow battery based on this concept can operate as a closed system. The flow battery architecture has scaling advantages over solid electrode batteries for large scale energy storage.

Small organic molecule based flow battery

The present invention provides novel synthetic methods for making acyclic secondary amines by reacting an azide with a compound bearing one or more C&#x2014;H groups, catalyzed by a Fe-dipyrromethene complex. The acyclic secondary amines are thought to be formed through an intermolecular nitrene transfer. Also provided herein are methods of synthesizing protected (e.g., Boc- or Fmoc-protected) cyclic secondary amines (e.g., 5-, 6-, and 7-membered cyclic secondary amines) by reacting an azide that bears one or more C&#x2014;H groups, catalyzed by a Fe-dipyrromethene complex. The protected cyclic secondary amines are thought to be formed through an intramolecular nitrene transfer and may be subsequently deprotected to yield cyclic secondary amines.

Synthesis of acyclic and cyclic amines using iron-catalyzed nitrene group transfer

Growing community of inventors

Cambridge, MA, United States of America

Theodore Alexander Betley