Density functional theory-supported studies of structural and electronic   properties of substituted-phenol derivatives synthesized by efficient O- or   C-arylation via Chan--Lam or Suzuki cross-coupling reactions

Hafiz Mansoor IKRAM; Nasir RASOOL; Muhammad Ali HASHMI; Muhammad Arfan ANJUM; Kulsoom Ghulam ALI; Muhammad ZUBAIR; Gulraiz AHMAD; Tariq MAHMOOD

Makale detayları

Density functional theory-supported studies of structural and electronic properties of substituted-phenol derivatives synthesized by efficient O- or C-arylation via Chan--Lam or Suzuki cross-coupling reactions

Yazarlar:

Hafiz Mansoor IKRAM | Nasir RASOOL | Muhammad Ali HASHMI | Muhammad Arfan ANJUM | Kulsoom Ghulam ALI | Muhammad ZUBAIR | Gulraiz AHMAD | Tariq MAHMOOD

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2019 Vol.43 Issue 5, pp.1306-1321

Belge Tipi:

Makale

Yayın Tarihi:

9/2019

Belge Dili:

İngilizce

Document ID (Org No.):

2000725572

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

The present study reports the efficient synthesis and   computational studies of the structural and electronic properties of some   interesting substituted phenol derivatives. Efficient and versatile   procedures to synthesize a series of diaryl ether derivatives   (2a-2c, 4a-4h) and bis-arylated   products (5a-5c) are described. In this manuscript, using   the commercially available starting material 1 and 3, a   1-step approach was developed by means of Cu(II)-mediated Chan-Lam and   Pd-catalyzed Suzuki cross-coupling reactions to synthesize diaryl ether and   bis-arylated products with moderate to good yields. The starting   substrates, 2-bromo-4-methylphenol 1 or 2,4-dibromophenol   3, were both treated with several arylboronic acids, which led to   the development of new carbon-oxygen bonds through Chan--Lam reactions. In   addition, the hydroxyl group of 2,4-dibromophenol 3 was protected   with isopropyl bromide to produce 4, which was then treated with   arylboronic acids to synthesize the corresponding bis-arylated products   through Suzuki cross-coupling reactions. Density functional theory   calculations provided insight into the structural and electronic properties   of the synthesized compounds. An analysis of the frontier orbitals and other   reactivity descriptors, including the ionization potential, electron   affinity, chemical hardness, electronic chemical potential, and   electrophilicity index, is presented, which shows that compound 4c   was the most reactive, while 4f and h were the most   stable.

Makale detayları

Density functional theory-supported studies of structural and electronic properties of substituted-phenol derivatives synthesized by efficient O- or C-arylation via Chan--Lam or Suzuki cross-coupling reactions

Yazarlar: Hafiz Mansoor IKRAM | Nasir RASOOL | Muhammad Ali HASHMI | Muhammad Arfan ANJUM | Kulsoom Ghulam ALI | Muhammad ZUBAIR | Gulraiz AHMAD | Tariq MAHMOOD

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2019 Vol.43 Issue 5, pp.1306-1321

Belge Tipi: Makale

Yayın Tarihi: 9/2019

Belge Dili: İngilizce

Document ID (Org No.): 2000725572

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Hafiz Mansoor IKRAM | Nasir RASOOL | Muhammad Ali HASHMI | Muhammad Arfan ANJUM | Kulsoom Ghulam ALI | Muhammad ZUBAIR | Gulraiz AHMAD | Tariq MAHMOOD

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2019 Vol.43 Issue 5, pp.1306-1321

Belge Tipi:

Makale

Yayın Tarihi:

9/2019

Belge Dili:

İngilizce

Document ID (Org No.):

2000725572

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527