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2007 C-C bond formation O 0282 Palladium-Catalyzed Alkylation of sp 2 and sp 3 C—H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C—H Activation Pathways. — The first protocol is presented for Pd-catalyzed alkylation of sp 2 and sp 3 C—H bonds with non-toxic methylboroxine (II) or alkylboronic acids (IV) using pyridine as directing group. The method avoids the use of toxic organotin reagents. A wide range of func- tional groups is tolerated including ether, ester, alcohol as well as vinyl groups. — (CHEN, X.; GOODHUE, C. E.; YU*, J.-Q.; J. Am. Chem. Soc. 128 (2006) 39, 12634-12635; Dep. Chem., Brandeis Univ., Waltham, MA 02454, USA; Eng.) — Mischke 06- 053

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Page 1: Palladium-Catalyzed Alkylation of sp2 and sp3 C—H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C—H Activation Pathways

2007

C-C bond formationO 0282 Palladium-Catalyzed Alkylation of sp2 and sp3 C—H Bonds with Methylboroxine

and Alkylboronic Acids: Two Distinct C—H Activation Pathways. — The first protocol is presented for Pd-catalyzed alkylation of sp2 and sp3 C—H bonds with non-toxic methylboroxine (II) or alkylboronic acids (IV) using pyridine as directing group. The method avoids the use of toxic organotin reagents. A wide range of func-tional groups is tolerated including ether, ester, alcohol as well as vinyl groups. — (CHEN, X.; GOODHUE, C. E.; YU*, J.-Q.; J. Am. Chem. Soc. 128 (2006) 39, 12634-12635; Dep. Chem., Brandeis Univ., Waltham, MA 02454, USA; Eng.) — Mischke

06- 053

Page 2: Palladium-Catalyzed Alkylation of sp2 and sp3 C—H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C—H Activation Pathways

2007


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