887027-36-3

Basic information

• Product Name: methyl α-diazo-α-(2-fluorophenyl)acetate
• Synonyms: methyl α-diazo-α-(2-fluorophenyl)acetate
• CAS NO: 887027-36-3
• Molecular Weight: 194.165
• Mol File: 887027-36-3.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: methyl α-diazo-α-(2-fluorophenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl α-diazo-α-(2-fluorophenyl)acetate(887027-36-3)
• EPA Substance Registry System: methyl α-diazo-α-(2-fluorophenyl)acetate(887027-36-3)

Safety Data

• Hazardous Substances Data: 887027-36-3(Hazardous Substances Data)

Upstream product

• 451-82-1 (2-fluorophenyl)acetic acid 
• 57486-67-6 methyl o-fluorophenylacetate 

Downstream Products

• 132115-73-2 methyl 2-fluoro-α-oxo-benzeneacetate 
• 1162672-00-5 methyl 1-(2-fluorophenyl)-2-phenylcycloprop-2-ene-1-carboxylate 

Relevant articles and documents

Insertion of Diazo Esters into C-F Bonds toward Diastereoselective One-Carbon Elongation of Benzylic Fluorides: Unprecedented BF3Catalysis with C-F Bond Cleavage and Re-formation

Selective transformation of C-F bonds remains a significant goal in organic chemistry, but C-F insertion of a one-carbon-atom unit has never been established. Herein we report the BF3-catalyzed formal insertion of diazo esters as one-carbon-atom sources into C-F bonds to accomplish one-carbon elongation of benzylic fluorides. A DFT calculation study revealed that the BF3 catalyst could contribute to both C-F bond cleavage and re-formation. This elongation provided α-fluoro-α,β-diaryl esters with a high level of diastereoselectivity. Various benzylic fluorides and diazo esters were applicable. The synthetic utility of this method was demonstrated by the synthesis of a fluoro analogue of a compound that is used as a transient receptor and potential canonical channel inhibitor.

Borane catalysed cyclopropenation of arylacetylenes

Triarylboranes have gained substantial attention as catalysts for C-C bond forming reactions due to their remarkable catalytic activities. Herein, we report B(C6F5)3catalysed cyclopropenation of a wide variety of arylacetylenes using donor-acceptor diazoesters. A mild reaction protocol has been developed for the synthesis of functionalised cyclopropenes (33 examples) in good to excellent yields.

Photochemical Doyle-Kirmse Reaction: A Route to Allenes

This Letter describes the metal-free, blue-light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yield. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.