MIT Chemistry Directory

Timothy F Jamison

Department Head and Robert R. Taylor Prof

The unifying theme of our research is the discovery and application of new reactions for organic synthesis.  Many of the transformations we target are based on common structural motifs or functional group patterns present in molecules provided to us by nature.

Developing effective and reliable continuous flow protocols to improve reaction yield, selectivity and minimize safety risks relative to batch conditions. Included are continuous flow protocols to prepare b-amino alcohols, tetrazoles, asymmetric ketones, cyclic carbonates and amide bonds as well as DIBAL-H reductions of esters to aldehydes, oxidation of alcohols and aldehydes, hydrogen-free alkene reductions, couplings (Ullmann condensations, Sonogashira couplings) and a variety of transformations mediated by photoredox catalysis.

Streamlining multi-step processes: telescoping two or three step reactions into a single, continuous and uninterrupted reactor network to circumvent the need for isolation and/or purification of intermediates. Some examples include developing (a) a continuous protocol for the two-carbon homologation of esters to prepare (a) β-unsaturated esters with high yield and selectivity;  (b) 2-functionalized phenols via benzyne-mediated in-line generation of arylmagnesium intermediates and aerobic oxidation; (c) developing a three-step continuous flow system which integrates in-line isocyanide formation and photochemical cyclization for preparing quinoxaline derivatives and (d) a two-step glycosylation and deprotection sequence to prepare 5’-deoxyribonucleoside pharmaceuticals. 

Designing integrated continuous manufacturing strategies for preparing active pharmaceutical ingredients. Within a broader context, I also been involved in developing end-to-end manufacturing processes which handle a variety of intermediate reactions, separations, crystallizations as well as drying and formulation to generate active pharmaceutical ingredients in one controlled process.

Nickel–Catalyzed Carbon–Carbon Bond Formation.  The majority of the transformations under investigation are carbon–carbon bond–forming reactions promoted by nickel catalysts. We have discovered a variety of coupling reactions to join a number of different functional groups in highly regio–, stereo– and enantioselective fashion depending on the nature of the supporting ligands on nickel.

Epoxide–Opening Cascades.  Over two decades ago, Koji Nakanishi proposed a provocative explanation for the structural and stereochemical similarities found across the ladder polyether family of natural products – the transformation of a polyepoxide into a ladder polyether via a cascade of epoxide–opening events. An ongoing effort in our group is the replication or emulation of such cascades. One aim is the efficient synthesis of these extremely complex natural products. In addition, we hope that our explorations into a diverse set of epoxide–opening cyclizations and cascades will shed further light on the fundamental feasibility of the Nakanishi’s hypothesis.


Target–Oriented Synthesis.  In order to test the scope and the utility of newly developed methods, we strive to employ them in the total synthesis of natural products. Often these products are the original inspiration for the development of these methods. For example, we have found that nickel–catalyzed reactions are compatible with a wide array of functional groups, making them useful in complex settings, such as fragment coupling or macrocyclization operations at a late stage in synthesis. 



Contact Information

t: 6172532135





Administrative Assistant

Emrick Elias (Headquarters)


Tel: (617) 258-7492

Room 18-393
77 Massachusetts Ave.
Cambridge, MA 02139

Nancy Parkinson (Research)


Tel: (617) 253-1830

Room 18-481
77 Massachusetts Ave.
Cambridge, MA 02139