“Carbon‐Centered Radical Addition to O=C of Amides or Esters as a Route to C‐O Bond Formations” Remains Elusive

Author:

Metzger Jürgen O.1ORCID

Affiliation:

1. Institute of ChemistryUniversity of Oldenburg 26111 Oldenburg Germany

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

Reference25 articles.

1. Carbon-Centered Radical Addition to OC of Amides or Esters as a Route to CO Bond Formations

2. Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary α-Carbonyl Alkyl Bromides

3. Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary α-Carbonyl Alkyl Bromides

4. The yield was 86 % with 2 equivalents of acetanilide added [2]and 65 % without acetanilide added (personal communication by C. Liu 14.4.2015).

5. The results of the calculations are given in Figure 2 of reference [1] and show clearly that path A (Scheme 3) may not be feasible. The free energy of activation of the claimed cyclization of3aIto3aIIis very similar as for the back reaction of3aIto2aI. Moreover the free energy of activation of the bimolecular trapping reaction of3 aIIto3aIIIand finally to product3 awas not considered and is expected to be some 10 kcal mol−1. Thus the back reaction would dominate and2aIwould initiate the polymerization of substrate2.

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