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. 2013 Aug 26;52(35):9316-9.
doi: 10.1002/anie.201304443. Epub 2013 Jul 5.

Rhodium-catalyzed boron arylation of 1,2-azaborines

Gabriel E Rudebusch  1 , Lev N Zakharov, Shih-Yuan Liu
Affiliations

Rhodium-catalyzed boron arylation of 1,2-azaborines

Gabriel E Rudebusch et al. Angew Chem Int Ed Engl. .

Abstract

A Sn-phony in B!: BN isosteres of biphenyl compounds are prepared through Rh-catalyzed cross-coupling between 2-chloro-1,2-azaborines and arylstannanes (see scheme). The synthetic method should enable investigations of structure–activity relationships (SARs) by expanding the chemical space of the pharmaceutically relevant biphenyl structure through BN/CC isosterism.

Keywords: azaborines; biphenyl; boron; heterocycles; isosterism.

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Figures

Figure 1
Figure 1
31P NMR spectra of the reaction between C′ and 1 a. P ~P =(S)-BINAP.
Scheme 1
Scheme 1
Biphenyl motif and its BN isostere. FG =functional group.
Scheme 2
Scheme 2
Synthesis of BN biphenyls through Rh-catalyzed addition of arylstannanes. The yields of isolated products are given as the average of two runs. [a] 48 h reaction time.
Scheme 3
Scheme 3
Synthesis of BN felbinac (5). Thermal ellipsoids of 4 drawn at the 35% probability level. TBS =tert-butyldimethylsilyl, TMS =trime-thylsilyl.
Scheme 4
Scheme 4
Proposed mechanism of the Rh-catalyzed addition of aryl-stannanes to B-Cl-substituted 1,2-azaborines.
See this image and copyright information in PMC

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