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简介 Organic research lab focusing on mechanism, synthesis, and catalysis

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实验室简介

Our research consists of both mechanistic and synthetic studies in organic chemistry with an emphasis on in-depth mechanistic understanding. In particular, we focus on the key reactive intermediates in important reactions, wherein the elucidation of their structure, formation mechanism, and reaction pattern are the core content of our research. Since 2014, we have been working on several representative reaction systems, and our studies have provided useful mechanistic insights that changed the established cognition of related fields and inspired the design of new reactions and catalysts.

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Lei Jiao

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Chemistry

Background: Diboron(4) compounds were prevalently employed in the borylation reactions. We have discovered that pyridine derivatives could catalyze the transition-metal-free borylation reaction of aryl halides with diboron(4) compounds. Detailed mechanistic study revealed an unprecedented reaction mode of pyridine and diboron(4) in the presence of an alcoholate to generate a novel N-boryl pyridyl anion key intermediate, which was found to enable a series of new reactions that constitute a unique pyridine-diboron-base reaction system.

Significance: 1) The formation of N-boryl pyridyl anion and its masked form indicates a formal nucleophilic addition of a boryl anion equivalant to the N-site of pyridine, which represents an important addition to the known reaction mode of pyridine (Scheme 2A). 2) A new organocatalytic mode of pyridine was demonstrated, in which pyridine forms N-boryl pyridyl anion to mediate redox or nucleophilic catalysis under either thermo or photoexcitation conditions (Scheme 2B-D). 3) A new umpolung-type pyridine derivatization strategy was developed based on the formation of N-boryl pyridyl anion (Scheme 2E).

Natural product synthesis

Synthesis of alkaloids.

Cooperative olefin ligands

Cooperative (or non-innocent) ligands

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