Phenylboronic Acid (PBA): A Versatile Chemical in Synthetic Organic Chemistry

Content Provider	Semantic Scholar
Author	Bao, Zhi-Jian
Copyright Year	2006
Abstract	s (A) Suzuki couplings1,2 of indoles3 with phenylboronic acids gave the products in high yields, which were unaffected by Boc or Tos protection at the heterocyclic nitrogen. (B) Amengual et al. first turned our attention to the coupling of boronic acids with either styrene or 2-vinylpyridine.4 The addition of various boronic acids to styrene and 2-vinylpyridine was realized with high selectivity and yield. (C) PBA is used in the ring-opening reaction of epoxy sulfides in benzene, which has been demonstrated to occur stereospecifically via episulfonium ions, i.e, with double inversion of the configuration, giving rise to phenylboronic esters of 2,3-diols5 in quantitative yields. (D) Yan et al. reported on the development of an arylboronic acid as protecting group for diols. Both protection and deprotection can be accomplished under mild conditions with quantitative conversion (yield: 91–95%). N R1 + X2 R2 Suzuki coupling N R1 X1 R 2 X1 = Br, B(OH)2 or Bpin R1 = H, Boc, Tos X2 = Br, B(OH)2, or Bpin R2 = 4-Me, 4-OMe, or 2-Me, 2-OMe X + ArB(OH)2 Rh(cod)Cl/TPPTS Na2CO3, 80 °C, 12 h Ar Ph or Ar C5H4N X = C, N PH2 NaO3S TPPTS = X = C
Starting Page	2679
Ending Page	2680
Page Count	2
File Format	PDF HTM / HTML
DOI	10.1055/s-2006-951472
Alternate Webpage(s)	https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-2006-951472.pdf
Alternate Webpage(s)	https://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-951472.pdf
Alternate Webpage(s)	https://doi.org/10.1055/s-2006-951472
Volume Number	2006
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article