ConspectusBridged and fused rings are commonly found in biologically important molecules. Current tactics to construct these ring systems are primarily based on stepwise ring formation (i.e., making...

While Catellani reactions have become increasingly important for arene functionalizations, they have been solely catalyzed by palladium. Here we report the first nickel-catalyzed Catellani-type...

Alkyl halides are versatile precursors to access diverse functional groups (FGs). Due to their lability, the development of surrogates for alkyl halides is strategically important for complex...

1,2-Azaborines, a unique class of BN-isosteres of benzene, have attracted great interest across several fields. While significant advancements have been made in the postfunctionalization of 1,2-aza...

Given the emerging demand to “escape from flatland” for drug discovery, synthetic methods that can efficiently construct complex three-dimensional structures with multi-stereocenters become increas...

Two members of the University of Chicago faculty have been elected to the American Academy of Arts and Sciences, one of the nation’s oldest and most prestigious honorary societies.

Transition-metal-catalyzed C–C activation has become synthetically valuable; however, it rarely involves single-electron downstream processes. To expand the repertoire of C–C activation, here we...

Boron-homologation reactions represent an efficient and programmable approach to prepare alkylboronates, which are valuable and versatile synthetic intermediates. The typical boron-homologation...

Direct functionalization of carbonyl β C–H bonds without using directing groups has not been a trivial task, and it is even more challenging to realize the corresponding atom-economical transformat...

Site-selective C–C bond formation through the direct coupling of C(sp3)–H bonds with unsaturated hydrocarbons represents an atom-economical and redox-neutral way to functionalize chemically inert...

The introduction of secondary amines at the aryl iodide ortho position by the palladium/norbornene (Pd/NBE) catalysis has been developed, which leads to versatile synthetic applications, such as...

Scalable fabrication of graphene nanoribbons with narrow band gaps has been a nontrivial challenge. Here, we have developed a simple approach to access narrow band gaps using hybrid edge structures....

A new reaction mode of palladium/norbornene (Pd/NBE) cooperative catalysis was developed involving coupling of two different carbon-based electrophiles for vicinal difunctionalization of five-membe...

Synthesis of bridged scaffolds via Type II cyclization constitutes substantial challenges due to the intrinsic ring strain accumulated in reaction transition states. Catalytic enantioselective Type...

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C–C cleavage to remove the acyl moiety, followed...

A photoinduced palladium-catalyzed desaturation method that is suitable for converting the linear amides to their α,β-unsaturated counterparts is reported. The reaction does not require strong...

A redox-neutral, heavy-metal-free approach has been developed to realize deacylative thiolation of common ketones, which provides a unique method to introduce thioether groups site-specifically to...

Watch this JACS Video Bytes summary of the article "Escape from Palladium: Nickel-Catalyzed Catellani Annulation" by Jingfeng Huo, Yue Fu, Melody J. Tang, Pe...

An unusual (4+1), instead of a normal (4+2), cycloaddition has been developed between benzocyclobutenones and styrene-type alkenes via the Rh-catalyzed C−C activation, which provides a distinct...

Here, we describe the development of a Rh-catalyzed intramolecular one-carbon homologation of unstrained aryl ketones through a formal 1,1-insertion process of olefins, enabled by temporary directing...

While enormous progress has been achieved in synthesizing atomically precise graphene nanoribbons (GNRs), the preparation of GNRs with a fully predetermined length and monomer sequence remains an...

Catalytic activation of unstrained and nonpolar C–C bonds remains a largely unmet challenge. Here, we describe our detailed efforts in developing a rhodium-catalyzed hydrogenolysis of unstrained...

Here we report the total synthesis of phainanoid A, a unique dammarane-type triterpenoid (DTT), using an unusual bidirectional synthetic strategy. It features two transition-metal-mediated highly...

An unexpected ortho-Heck reaction has been discovered during the study of palladium/norbornene (Pd/NBE) catalysis. Under the Catellani reaction conditions in the presence of lithium salts and...

A palladium/norbornene-catalyzed vicinal difunctionalization of enol triflates has been developed for rapid, modular and regioselective synthesis of multisubstituted acrylamides from simple ketones....

Tetrahydrobenzo[b]azepines (THBAs) are commonly found in many bioactive compounds; however, the modular preparation of functionalized THBAs remains challenging to date. Here, we report a straightfo...

A distal-selective alkenyl C–H arylation method is reported through a directed palladium/norbornene (Pd/NBE) cooperative catalysis. The key is to use an appropriate combination of the directing group...

Arenes with four different contiguous substituents, i.e. 1,2,3,4-tetrasubstituted arenes, are commonly found in bioactive compounds, but they are nontrivial to access via conventional methods....