Abstract
A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 7754-7755 |
| Number of pages | 2 |
| Journal | Journal of the American Chemical Society |
| Volume | 125 |
| Issue number | 26 |
| DOIs | |
| State | Published - Jul 2 2003 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
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The reaction of thio acids with azides : A new mechanism and new synthetic applications. / Shangguan, Ning; Katukojvala, Sreenivas; Greenberg, Rachel; Williams, Lawrence.
In: Journal of the American Chemical Society, Vol. 125, No. 26, 02.07.2003, p. 7754-7755.Research output: Contribution to journal › Article
TY - JOUR
T1 - The reaction of thio acids with azides
T2 - A new mechanism and new synthetic applications
AU - Shangguan, Ning
AU - Katukojvala, Sreenivas
AU - Greenberg, Rachel
AU - Williams, Lawrence
PY - 2003/7/2
Y1 - 2003/7/2
N2 - A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.
AB - A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.
UR - http://www.scopus.com/inward/record.url?scp=0038788894&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0038788894&partnerID=8YFLogxK
U2 - 10.1021/ja0294919
DO - 10.1021/ja0294919
M3 - Article
C2 - 12822965
AN - SCOPUS:0038788894
VL - 125
SP - 7754
EP - 7755
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 26
ER -