144061-77-8Relevant academic research and scientific papers
Continuous synthesis of organozinc halides coupled to Negishi reactions
Alonso, Nerea,Miller, L. Zane,De M. Muoz, Juan,Alczar, Jesus,McQuade, D. Tyler
supporting information, p. 3737 - 3741 (2015/01/16)
The Negishi cross-coupling is a powerful C-C bond forming reaction. The method is less commonly used relative to other cross-coupling methods in part due to lack of availability of organozinc species. While organozinc species can be prepared, problems wit
AN INVESTIGATION OF THE INFLUENCE OF HALOARENES AND HETARYLACETONITRILES ON THE COMPETITION BETWEEN POSSIBLE ARYNE ARYLATION AND TANDEM ADDITION-REARRANGEMENT PATHWAYS
Deshmukh, A. Rakeeb,Morgan, Matt,Tran, Long,Zhang, Hongming,Dutt, Mahesh,Biehl, Edward R.
, p. 1239 - 1249 (2007/10/02)
Attempts to extend the LDA-mediated 1-aminoisoquinoline arynic synthesis to 1,2-dibromo-3,4,5,6-tetramethylbenzene (1a) and the hetarylacetonitriles 2- (2a) and 3-pyridylacetonitrile (2b), 2- (2c) and 3-thiopheneacetonitrile (2d), and 2-benzimidizoylacetonitrile (2e) failed; only rearranged 2-hetarylmethyl-3,4,5,6-tetramethylbenzonitriles (3aa-3ae) were obtained.Additionally, the reaction of 1-chloro-2,5-dimethylbenzene (1b), 2-bromo-4-methylanisole (1c), bromobenzene (1d), 2-bromoanisole (1e), and 1-bromo-2,5-dimethoxybenzene (1f) with 2a-e gave rearranged nitriles (3) by the tandem addition-rearrangement aryne pathway and/or aryne arylated nitriles (4) by the aryne arylation pathway.By evaluating product 3:4 ratios from these reactions, an assessment of the influence of the nature of the haloarenes and hetarylacetonitriles on the competing tandem addition-rearrangement and aryne arylation pathways was made, which showed that the preference of the haloarenes for the rearrangement pathway to be 1a ca. 1b > 1c > 1d > 1e > 1f and that for the hetarylacetonitriles to be 2c ca. 2d > 2b > 2a > 2e.An explanation in terms of the influence of the haloarene substituents on the ring-closure step of the rearrangement pathway and the heterocyclic ring of the hetarylacetonitrile on the proton abstraction step of the alternate aryne arylation pathway is presented.
