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4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group for the Pd(II)-Catalyzed Arylation/Oxygenation of sp2/sp3 β-C-H Bonds of Carboxamides.
J Org Chem. 2016 12 16; 81(24):12143-12168.JO

Abstract

In this paper, we report 4-amino-2,1,3-benzothiadiazole (ABTD) as a new bidentate directing group for the Pd(II)-catalyzed sp2/sp3 C-H activation/functionalization of various aliphatic/alicyclic/aromatic carboxamide systems. The Pd(II)-catalyzed, ABTD-directed sp3 C-H arylation/acetoxylation of aliphatic- and alicyclic carboxamides afforded the corresponding β-C-H arylated/acetoxylated carboxamides. The Pd(II)-catalyzed, ABTD-directed sp3 C-H arylation of cyclobutanecarboxamide with different aryl iodides afforded the corresponding bis β-C-H arylated cyclobutanecarboxamides having all-cis stereochemistry with a high degree of stereocontrol. The Pd(II)-catalyzed, ABTD-directed arylation/benzylation/acetoxylation/alkoxylation of ortho C(sp2)-H bonds of various benzamides afforded the corresponding ortho C-H arylated/benzylated/oxygenated benzamides. The observed regio- and stereoselectivity in the Pd(II)-catalyzed, ABTD-directed arylation/benzylation of aliphatic/alicyclic carboxamides and benzamides were ascertained from the X-ray structures of representative compounds 5g (bis-β-C(sp3)-H arylated cyclobutanecarboxamide) and 7f (ortho C(sp2)-H arylated benzamide). A brief description on the efficiency, scope, and limitations of bidentate directing group ABTD is reported.

Authors+Show Affiliations

Reddy C
Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali , Manauli P.O., Sector 81, SAS Nagar, Knowledge City, Mohali, Punjab 140306, India.
Bisht N
Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali , Manauli P.O., Sector 81, SAS Nagar, Knowledge City, Mohali, Punjab 140306, India.
Parella R
Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali , Manauli P.O., Sector 81, SAS Nagar, Knowledge City, Mohali, Punjab 140306, India.
Babu SA
Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali , Manauli P.O., Sector 81, SAS Nagar, Knowledge City, Mohali, Punjab 140306, India.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

27978723

Citation

Reddy, Chennakesava, et al. "4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group for the Pd(II)-Catalyzed Arylation/Oxygenation of Sp2/sp3 β-C-H Bonds of Carboxamides." The Journal of Organic Chemistry, vol. 81, no. 24, 2016, pp. 12143-12168.
Reddy C, Bisht N, Parella R, et al. 4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group for the Pd(II)-Catalyzed Arylation/Oxygenation of sp2/sp3 β-C-H Bonds of Carboxamides. J Org Chem. 2016;81(24):12143-12168.
Reddy, C., Bisht, N., Parella, R., & Babu, S. A. (2016). 4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group for the Pd(II)-Catalyzed Arylation/Oxygenation of sp2/sp3 β-C-H Bonds of Carboxamides. The Journal of Organic Chemistry, 81(24), 12143-12168.
Reddy C, et al. 4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group for the Pd(II)-Catalyzed Arylation/Oxygenation of Sp2/sp3 β-C-H Bonds of Carboxamides. J Org Chem. 2016 12 16;81(24):12143-12168. PubMed PMID: 27978723.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group for the Pd(II)-Catalyzed Arylation/Oxygenation of sp2/sp3 β-C-H Bonds of Carboxamides. AU - Reddy,Chennakesava, AU - Bisht,Narendra, AU - Parella,Ramarao, AU - Babu,Srinivasarao Arulananda, Y1 - 2016/12/06/ PY - 2016/12/17/entrez PY - 2016/12/17/pubmed PY - 2016/12/17/medline SP - 12143 EP - 12168 JF - The Journal of organic chemistry JO - J Org Chem VL - 81 IS - 24 N2 - In this paper, we report 4-amino-2,1,3-benzothiadiazole (ABTD) as a new bidentate directing group for the Pd(II)-catalyzed sp2/sp3 C-H activation/functionalization of various aliphatic/alicyclic/aromatic carboxamide systems. The Pd(II)-catalyzed, ABTD-directed sp3 C-H arylation/acetoxylation of aliphatic- and alicyclic carboxamides afforded the corresponding β-C-H arylated/acetoxylated carboxamides. The Pd(II)-catalyzed, ABTD-directed sp3 C-H arylation of cyclobutanecarboxamide with different aryl iodides afforded the corresponding bis β-C-H arylated cyclobutanecarboxamides having all-cis stereochemistry with a high degree of stereocontrol. The Pd(II)-catalyzed, ABTD-directed arylation/benzylation/acetoxylation/alkoxylation of ortho C(sp2)-H bonds of various benzamides afforded the corresponding ortho C-H arylated/benzylated/oxygenated benzamides. The observed regio- and stereoselectivity in the Pd(II)-catalyzed, ABTD-directed arylation/benzylation of aliphatic/alicyclic carboxamides and benzamides were ascertained from the X-ray structures of representative compounds 5g (bis-β-C(sp3)-H arylated cyclobutanecarboxamide) and 7f (ortho C(sp2)-H arylated benzamide). A brief description on the efficiency, scope, and limitations of bidentate directing group ABTD is reported. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/27978723/4_Amino_213_benzothiadiazole_as_a_Removable_Bidentate_Directing_Group_for_the_Pd_II__Catalyzed_Arylation/Oxygenation_of_sp2/sp3_β_C_H_Bonds_of_Carboxamides_ DB - PRIME DP - Unbound Medicine ER -
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