Stephen L. Buchwald
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View article: Deciphering the alteration of MAP2 interactome caused by a schizophrenia-associated phosphorylation
Deciphering the alteration of MAP2 interactome caused by a schizophrenia-associated phosphorylation Open
Microtubule-associated protein 2 (MAP2) is a crucial regulator of dendritic structure and neuronal function, orchestrating diverse protein interactions within the microtubule network. We have shown MAP2 is hyperphosphorylated at serine 178…
View article: Copper-Catalyzed Amination of Aryl Chlorides under Mild Reaction Conditions
Copper-Catalyzed Amination of Aryl Chlorides under Mild Reaction Conditions Open
We report a mild method for the copper-catalyzed amination of aryl chlorides. Key to the success of the method was the use of highly sterically encumbered N1,N2-diaryl diamine ligands which resist cataly…
View article: Cu-Catalyzed Amination of Base-Sensitive Aryl Bromides and the Chemoselective N- and O-Arylation of Amino Alcohols
Cu-Catalyzed Amination of Base-Sensitive Aryl Bromides and the Chemoselective N- and O-Arylation of Amino Alcohols Open
We report a general and functional-group-tolerant method for the Cu-catalyzed amination of base-sensitive aryl bromides including substrates possessing acidic functional groups and small five-membered heteroarenes. The results presented he…
View article: Automated Flow Synthesis of Artificial Heme Enzymes for Enantioselective Biocatalysis
Automated Flow Synthesis of Artificial Heme Enzymes for Enantioselective Biocatalysis Open
The remarkable efficiency with which enzymes catalyze small molecule reactions has driven their widespread application in organic chemistry. Here, we employ automated fast-flow solid-phase synthesis to access full-length enzymes without re…
View article: CuH-Catalyzed Regio- and Enantioselective Formal Hydroformylation of Vinyl Arenes
CuH-Catalyzed Regio- and Enantioselective Formal Hydroformylation of Vinyl Arenes Open
A highly enantioselective formal hydroformylation of vinyl arenes enabled by copper hydride (CuH) catalysis is reported. Key to the success of the method was the use of the mild Lewis acid zinc triflate to promote the formation of oxocarbe…
View article: Miquel Pericàs – an Outstanding Scientist and a Great Friend
Miquel Pericàs – an Outstanding Scientist and a Great Friend Open
From left to right: Miquel Pericàs, Laura Herrero (Ruben Martin's wife), Anne-Liese Pericàs, Steve Buchwald, Ruben Martin I first met Miquel Pericàs when he came to MIT to visit in the mid-1990s and to check on the progress of his student,…
View article: Room‐Temperature Copper‐Catalyzed Etherification of Aryl Bromides
Room‐Temperature Copper‐Catalyzed Etherification of Aryl Bromides Open
We disclose the development of a Cu‐catalyzed C−O coupling method utilizing a new N 1 , N 2 ‐diarylbenzene‐1,2‐diamine ligand, L8 . Under optimized reaction conditions, structurally diverse aryl and heteroaryl bromides underwent efficient …
View article: Room-Temperature Cu-Catalyzed Etherification of Aryl Bromides
Room-Temperature Cu-Catalyzed Etherification of Aryl Bromides Open
Transition-metal-catalyzed C–O coupling reactions of aryl halides and alcohols represent a useful alternative to classical aromatic substitution methods due to their improved functional group tolerance and substrate scope. Despite these be…
View article: Site-Specific Antibody Prodrugs via S-Arylation: A Bioconjugation Approach Toward Masked Tyrosine Analogues
Site-Specific Antibody Prodrugs via S-Arylation: A Bioconjugation Approach Toward Masked Tyrosine Analogues Open
The utility of antibody therapeutics is hampered by potential cross-reactivity with healthy tissue. Over the past decade, significant advances have been made in the design of activatable antibodies which increase, or create altogether, the…
View article: Stereoselective Synthesis of Trisubstituted Alkenes via Copper Hydride-Catalyzed Alkyne Hydroalkylation
Stereoselective Synthesis of Trisubstituted Alkenes via Copper Hydride-Catalyzed Alkyne Hydroalkylation Open
Alkenes are ubiquitous in organic chemistry, yet many classes of alkenes remain challenging to access by current synthetic methodology. Herein, we report a copper hydride-catalyzed approach for the synthesis of Z-configured trisubst…
View article: Electrophile Scanning Reveals Reactivity Hotspots for the Design of Covalent Peptide Binders
Electrophile Scanning Reveals Reactivity Hotspots for the Design of Covalent Peptide Binders Open
Protein–protein interactions (PPIs) are intriguing targets in drug discovery and development. Peptides are well suited to target PPIs, which typically present with large surface areas lacking distinct features and deep binding pockets. To …
View article: CCDC 2005287: Experimental Crystal Structure Determination
CCDC 2005287: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Room-Temperature Cu-Catalyzed Amination of Aryl Bromides Enabled by DFT-Guided Ligand Design
Room-Temperature Cu-Catalyzed Amination of Aryl Bromides Enabled by DFT-Guided Ligand Design Open
Ullmann-type C-N coupling reactions represent an important alternative to well-established Pd-catalyzed approaches due to the differing reactivity and the lower cost of Cu. While the design of anionic Cu ligands, particularly those by Ma, …
View article: Abiotic peptides as carriers of information for the encoding of small-molecule library synthesis
Abiotic peptides as carriers of information for the encoding of small-molecule library synthesis Open
Encoding small-molecule information in DNA has been leveraged to accelerate the discovery of ligands for therapeutic targets such as proteins. However, oligonucleotide-based encoding is hampered by inherent limitations of information stabi…
View article: Studying Regioisomer Formation in the Pd‐Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification**
Studying Regioisomer Formation in the Pd‐Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification** Open
Pd‐catalyzed nucleophilic fluorination reactions are important methods for the synthesis of fluoroarenes and fluoroalkenes. However, these reactions can generate a mixture of regioisomeric products that are often difficult to separate. Whi…
View article: Studying Regioisomer Formation in the Pd‐Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification**
Studying Regioisomer Formation in the Pd‐Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification** Open
Pd‐catalyzed nucleophilic fluorination reactions are important methods for the synthesis of fluoroarenes and fluoroalkenes. However, these reactions can generate a mixture of regioisomeric products that are often difficult to separate. Whi…
View article: Pd-Catalyzed Amination of Base-Sensitive Five-Membered Heteroaryl Halides with Aliphatic Amines
Pd-Catalyzed Amination of Base-Sensitive Five-Membered Heteroaryl Halides with Aliphatic Amines Open
We report a versatile and functional-group-tolerant method for the Pd-catalyzed C-N cross-coupling of five-membered heteroaryl halides with primary and secondary amines, an important but underexplored transformation. Coupling reactions of …
View article: Replacement solvents for use in chemical synthesis
Replacement solvents for use in chemical synthesis Open
Replacement solvents for use in chemical synthesis include polymer-immobilized solvents having a flexible polymer backbone and a plurality of pendant groups attached onto the polymer backbone, the pendant groups comprising a flexible linki…
View article: Room Temperature Cu-Catalyzed Amination of Aryl Bromides Enabled by DFT-Guided Ligand Design
Room Temperature Cu-Catalyzed Amination of Aryl Bromides Enabled by DFT-Guided Ligand Design Open
Ullman-type C–N coupling reactions represent an important alternative to well-established Pd-catalyzed approaches due to the differing reactivity and the lower cost of Cu. While the design of anionic Cu ligands, particularly those by Ma, h…
View article: CCDC 2157585: Experimental Crystal Structure Determination
CCDC 2157585: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: A Great Chemist and Friend
A Great Chemist and Friend Open
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View article: Abiotic peptides for the encoding of small molecule synthesis
Abiotic peptides for the encoding of small molecule synthesis Open
Information storage in DNA forms the fundamental basis of cellular life, but inherent limitations of information stability and density hamper innovative applications such as data storage or drug discovery. Here, we establish abiotic peptid…
View article: A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis
A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis Open
α‐Stereogenic allyl metalloids are versatile synthetic intermediates which can undergo various stereocontrolled transformations. Most existing methods to prepare α‐stereogenic allyl metalloids involve multi‐step sequences that curtail the …
View article: A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis
A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis Open
α‐Stereogenic allyl metalloids are versatile synthetic intermediates which can undergo various stereocontrolled transformations. Most existing methods to prepare α‐stereogenic allyl metalloids involve multi‐step sequences that curtail the …
View article: Roadmap to Pharmaceutically Relevant Reactivity Models Leveraging High-Throughput Experimentation
Roadmap to Pharmaceutically Relevant Reactivity Models Leveraging High-Throughput Experimentation Open
The merger of High-Throughput Experimentation (HTE) and data science presents an opportunity to both accelerate and inspire innovations in synthetic chemistry. Similarly, developments in machine learning (ML) have enabled the distillation …
View article: Copper Hydride-Catalyzed Enantioselective Olefin Hydromethylation
Copper Hydride-Catalyzed Enantioselective Olefin Hydromethylation Open
The enantioselective installation of a methyl group onto a small molecule can result in the significant modification of its biological properties. While hydroalkylation of olefins represents an attractive approach to introduce alkyl substi…
View article: Copper Hydride-Catalyzed Enantioselective Olefin Hydromethylation
Copper Hydride-Catalyzed Enantioselective Olefin Hydromethylation Open
The enantioselective installation of a methyl group onto a small molecule can result in the significant modification of its biological properties. While hydroalkylation of olefins represents an attractive approach to introduce alkyl substi…
View article: Enantioselective Hydrocarbamoylation of Alkenes
Enantioselective Hydrocarbamoylation of Alkenes Open
The asymmetric hydroaminocarbonylation of olefins represents a straightforward approach for the synthesis of enantioenriched amides, but is hampered by the necessity to employ CO gas, often at elevated pressures. We herein describe, as an …
View article: Enantioselective Hydrocarbamoylation of Alkenes
Enantioselective Hydrocarbamoylation of Alkenes Open
The asymmetric hydroaminocarbonylation of olefins represents a straightforward approach for the synthesis of enantioenriched amides, but is hampered by the necessity to employ CO gas, often at elevated pressures. We herein describe, as an …