Structure and Reactivity of a Preactivated sp2-sp3 Diboron Reagent: Catalytic Regioselective Boration of α,β-Unsaturated Conjugated Compounds
Ming Gao; Steven B. Thorpe; Christian Kleeberg; Carla Slebodnick; Todd B. Marder; Webster L. Santos; Journal of Organic Chemistry 76 (2011) 3997–4007; doi:10.1021/jo2003488

data_4026298
_publ_contact_author_address
;
 Department of Chemistry 
   Virginia Tech 
   3101 Hahn Hall
   West campus Dr. 
   Blacksburg, VA  24061  USA
;
_publ_contact_author_email       wsantos@vt.edu
_publ_contact_author_fax         1(540)2313255
_publ_contact_author_name        'Webster L. Santos'
_publ_contact_author_phone       1(540)2315742
_publ_section_title
;
 Structure and Reactivity of a Preactivated sp2-sp3 Diboron Reagent:
 Catalytic Regioselective Boration of \a,\b-Unsaturated Conjugated
 Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3997
_journal_page_last               4007
_journal_paper_doi               10.1021/jo2003488
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C16 H32 B2 K N O5'
_chemical_formula_sum            'C16 H32 B2 K N O5'
_chemical_formula_weight         379.15
_chemical_name_common
;
 rearranged PDIPA diboron
;
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.8010(10)
_cell_angle_beta                 83.1700(10)
_cell_angle_gamma                69.7520(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8528(3)
_cell_length_b                   10.1429(3)
_cell_length_c                   10.9377(3)
_cell_measurement_reflns_used    8613
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.22
_cell_volume                     1018.12(5)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13552
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2006/1 (Bruker AXS), R(int)=0.0619 before correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method
'Crystallized from a solution of (DIPA)B-Bpin and KOtBu in THF at RT.'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.3101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                4272
_reflns_number_total             4906
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo2003488_si_002.cif
_cod_data_source_block           09srv365
_cod_database_code               4026298