TY - JOUR
T1 - Dirhodium-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles to 2,3-Dehydropiperazines
AU - Nutt, Michael J.
AU - Annear, Jack W.
AU - Jones, Kieran D.
AU - Flematti, Gavin R.
AU - Moggach, Stephen A.
AU - Stewart, Scott G.
PY - 2023/8/18
Y1 - 2023/8/18
N2 - The dirhodium(II)-catalyzed synthesis of a range of C2-substituted 2,3-dehydropiperazines using 1-mesyl-1,2,3-triazoles and β-haloalkylcarbamates is reported. The reaction is proposed to proceed through an α-imino rhodium carbene 1,3-insertion into N-H followed by a base-mediated cyclization. C-Substituted dehydropiperazines can also be conducted directly from terminal alkynes in a three-step, one-pot operation, forming the triazole in situ. This methodology has also been expanded to afford several 2,5-disubstituted 2,3-dehydropiperazines as well as a larger 4,5,6,7-tetrahydro-1H-1,4-diazepine derivative.
AB - The dirhodium(II)-catalyzed synthesis of a range of C2-substituted 2,3-dehydropiperazines using 1-mesyl-1,2,3-triazoles and β-haloalkylcarbamates is reported. The reaction is proposed to proceed through an α-imino rhodium carbene 1,3-insertion into N-H followed by a base-mediated cyclization. C-Substituted dehydropiperazines can also be conducted directly from terminal alkynes in a three-step, one-pot operation, forming the triazole in situ. This methodology has also been expanded to afford several 2,5-disubstituted 2,3-dehydropiperazines as well as a larger 4,5,6,7-tetrahydro-1H-1,4-diazepine derivative.
UR - http://www.scopus.com/inward/record.url?scp=85167782618&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c01259
DO - 10.1021/acs.joc.3c01259
M3 - Article
C2 - 37523269
AN - SCOPUS:85167782618
SN - 0022-3263
VL - 88
SP - 11968
EP - 11979
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -