Palladium Acyclic Diaminocarbene (ADC) Triflate Complexes as Effective Precatalysts for the Hiyama Alkynylation/Cyclization Reaction Yielding Benzofuran Compounds: Probing the Influence of the Triflate Co-Ligand in the One-Pot Tandem Reaction

Chandan Singh; A.P. Prakasham; Prasenjit Ghosh

doi:10.1002/slct.201803292

Palladium Acyclic Diaminocarbene (ADC) Triflate Complexes as Effective Precatalysts for the Hiyama Alkynylation/Cyclization Reaction Yielding Benzofuran Compounds: Probing the Influence of the Triflate Co-Ligand in the One-Pot Tandem Reaction

Chandan Singh
, A.P. Prakasham
, Prasenjit Ghosh

Research output: Contribution to journal › Article › Academic › peer-review

18 Citations (Scopus)

Abstract

Palladium acyclic diaminocarbene (ADC) complexes of the type cis-[(R¹NH)(R²)methylidene]Pd(OCOCF₃)₂(CNR¹) [R¹ = 2,4,6-(CH₃)₃C₆H₂: R² = NC₄H₈ (1); NC₅H₁₀ (2)] have been synthesized and structurally characterized. These 1 and 2 complexes are effective precatalysts for the one-pot tandem Hiyama alkynylation/cyclization reaction producing benzofuran compounds and, quite interestingly, higher yields of ca. 33−52 % were observed for the aryl triethoxysilylalkyne substrates as compared to that of ca. 15−21 % for the aliphatic triethoxysilylalkyne substrates. The 1 and 2 complexes were conveniently prepared by the salt metathesis reaction of the chloro derivatives with AgOCOCF₃ in excellent yields (ca. 84−94 %) under ambient conditions.

Original language	English
Pages (from-to)	329-336
Number of pages	8
Journal	ChemistrySelect
Volume	4
Issue number	1
DOIs	https://doi.org/10.1002/slct.201803292
Publication status	Published - 10 Jan 2019
Externally published	Yes

Keywords

acyclic diaminocarbene complexes (ADCs)
benzofuran derivatives
hiyama alkynylation/cyclization
one-pot tandem reactions
palladium

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@article{f4ded772be064209b82574c37c14ce28,

title = "Palladium Acyclic Diaminocarbene (ADC) Triflate Complexes as Effective Precatalysts for the Hiyama Alkynylation/Cyclization Reaction Yielding Benzofuran Compounds: Probing the Influence of the Triflate Co-Ligand in the One-Pot Tandem Reaction",

abstract = "Palladium acyclic diaminocarbene (ADC) complexes of the type cis-[(R1NH)(R2)methylidene]Pd(OCOCF3)2(CNR1) [R1 = 2,4,6-(CH3)3C6H2: R2 = NC4H8 (1); NC5H10 (2)] have been synthesized and structurally characterized. These 1 and 2 complexes are effective precatalysts for the one-pot tandem Hiyama alkynylation/cyclization reaction producing benzofuran compounds and, quite interestingly, higher yields of ca. 33−52 \% were observed for the aryl triethoxysilylalkyne substrates as compared to that of ca. 15−21 \% for the aliphatic triethoxysilylalkyne substrates. The 1 and 2 complexes were conveniently prepared by the salt metathesis reaction of the chloro derivatives with AgOCOCF3 in excellent yields (ca. 84−94 \%) under ambient conditions.",

keywords = "acyclic diaminocarbene complexes (ADCs), benzofuran derivatives, hiyama alkynylation/cyclization, one-pot tandem reactions, palladium",

author = "Chandan Singh and A.P. Prakasham and Prasenjit Ghosh",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = jan,

day = "10",

doi = "10.1002/slct.201803292",

language = "English",

volume = "4",

pages = "329--336",

journal = "ChemistrySelect",

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Singh, C, Prakasham, AP & Ghosh, P 2019, 'Palladium Acyclic Diaminocarbene (ADC) Triflate Complexes as Effective Precatalysts for the Hiyama Alkynylation/Cyclization Reaction Yielding Benzofuran Compounds: Probing the Influence of the Triflate Co-Ligand in the One-Pot Tandem Reaction', ChemistrySelect, vol. 4, no. 1, pp. 329-336. https://doi.org/10.1002/slct.201803292

Palladium Acyclic Diaminocarbene (ADC) Triflate Complexes as Effective Precatalysts for the Hiyama Alkynylation/Cyclization Reaction Yielding Benzofuran Compounds: Probing the Influence of the Triflate Co-Ligand in the One-Pot Tandem Reaction. / Singh, Chandan; Prakasham, A.P.; Ghosh, Prasenjit.
In: ChemistrySelect, Vol. 4, No. 1, 10.01.2019, p. 329-336.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Palladium Acyclic Diaminocarbene (ADC) Triflate Complexes as Effective Precatalysts for the Hiyama Alkynylation/Cyclization Reaction Yielding Benzofuran Compounds

T2 - Probing the Influence of the Triflate Co-Ligand in the One-Pot Tandem Reaction

AU - Singh, Chandan

AU - Prakasham, A.P.

AU - Ghosh, Prasenjit

PY - 2019/1/10

Y1 - 2019/1/10

N2 - Palladium acyclic diaminocarbene (ADC) complexes of the type cis-[(R1NH)(R2)methylidene]Pd(OCOCF3)2(CNR1) [R1 = 2,4,6-(CH3)3C6H2: R2 = NC4H8 (1); NC5H10 (2)] have been synthesized and structurally characterized. These 1 and 2 complexes are effective precatalysts for the one-pot tandem Hiyama alkynylation/cyclization reaction producing benzofuran compounds and, quite interestingly, higher yields of ca. 33−52 % were observed for the aryl triethoxysilylalkyne substrates as compared to that of ca. 15−21 % for the aliphatic triethoxysilylalkyne substrates. The 1 and 2 complexes were conveniently prepared by the salt metathesis reaction of the chloro derivatives with AgOCOCF3 in excellent yields (ca. 84−94 %) under ambient conditions.

AB - Palladium acyclic diaminocarbene (ADC) complexes of the type cis-[(R1NH)(R2)methylidene]Pd(OCOCF3)2(CNR1) [R1 = 2,4,6-(CH3)3C6H2: R2 = NC4H8 (1); NC5H10 (2)] have been synthesized and structurally characterized. These 1 and 2 complexes are effective precatalysts for the one-pot tandem Hiyama alkynylation/cyclization reaction producing benzofuran compounds and, quite interestingly, higher yields of ca. 33−52 % were observed for the aryl triethoxysilylalkyne substrates as compared to that of ca. 15−21 % for the aliphatic triethoxysilylalkyne substrates. The 1 and 2 complexes were conveniently prepared by the salt metathesis reaction of the chloro derivatives with AgOCOCF3 in excellent yields (ca. 84−94 %) under ambient conditions.

KW - acyclic diaminocarbene complexes (ADCs)

KW - benzofuran derivatives

KW - hiyama alkynylation/cyclization

KW - one-pot tandem reactions

KW - palladium

UR - https://www.scopus.com/pages/publications/85059868930

U2 - 10.1002/slct.201803292

DO - 10.1002/slct.201803292

M3 - Article

AN - SCOPUS:85059868930

SN - 2365-6549

VL - 4

SP - 329

EP - 336

JO - ChemistrySelect

JF - ChemistrySelect

IS - 1

ER -

Palladium Acyclic Diaminocarbene (ADC) Triflate Complexes as Effective Precatalysts for the Hiyama Alkynylation/Cyclization Reaction Yielding Benzofuran Compounds: Probing the Influence of the Triflate Co-Ligand in the One-Pot Tandem Reaction

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