Reversible Twisting of Primary Amides via Ground State N–C(O) Destabilization: Highly Twisted Rotationally Inverted Acyclic Amides
- Award ID(s):
- 1650766
- PAR ID:
- 10055412
- Date Published:
- Journal Name:
- Journal of the American Chemical Society
- Volume:
- 140
- Issue:
- 2
- ISSN:
- 0002-7863
- Page Range / eLocation ID:
- 727 to 734
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
This chapter provides a summary of the recent advances in direct transamidation and amidation reactions of activated amides and esters via transition- metal-catalyzed and transition-metal-free C(acyl)–N and C(acyl)–O bond cleavage as a new disconnection for the synthesis of amide bonds.more » « less
-
Cross-coupling reactions are among the most powerful C–C and C–X bond forming tools in organic chemistry. Traditionally, cross-coupling methods rely on the use of aryl halides or pseudohalides as electrophiles. In the past three years, decarbonylative cross-couplings of amides have emerged as an attractive method for the construction of a wide variety of carbon–carbon and carbon–heteroatom bonds, allowing for the synthetically-valuable functional group inter-conversion of the amide bond. These previously elusive reactions hinge upon selective activation of the N–C(O) acyl amide bond, followed by CO extrusion, in a formal double N–C/C–C bond activation, to generate a versatile aryl–metal intermediate as an attractive alternative to traditional cross-couplings of aryl halides and pseudohalides. In this perspective review, we present recent advances and key developments in the field of decarbonylative cross-coupling reactions of amides as well as discuss future challenges and potential applications for this exciting field.more » « less
An official website of the United States government

