Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters
Jacob W. Clary; Terry J. Rettenmaier; Rachel Snelling; Whitney Bryks; Jesse Banwell; W. Todd Wipke; Bakthan Singaram; Journal of Organic Chemistry 76 (2011) 9602–9610; doi:10.1021/jo201093u

data_4026749
_publ_contact_author_address     '398 PSB'
_publ_contact_author_email       clary@chemistry
_publ_contact_author_name        'Jacob Clary'
_publ_contact_author_phone       9-3479
_publ_section_title
;
 Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides
 under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of
 Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9602
_journal_page_last               9610
_journal_paper_doi               10.1021/jo201093u
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H32 Br2 Mg O4'
_chemical_formula_weight         472.55
_space_group_IT_number           94
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4n 2n'
_symmetry_space_group_name_H-M   'P 42 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7653(5)
_cell_length_b                   7.7653(5)
_cell_length_c                   17.0129(12)
_cell_measurement_reflns_used    5517
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      5.25
_cell_volume                     1025.88(12)
_computing_cell_refinement       'Bruker SAINT v7.34A'
_computing_data_collection       'Bruker APEX-II v2.1-4'
_computing_data_reduction        'Bruker SAINT v7.34A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       \w/2\q-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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0091
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11447
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    3.996
_exptl_absorpt_correction_T_max  0.3705
_exptl_absorpt_correction_T_min  0.2553
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       tablet
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.34(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0138P)^2^+0.3479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0424
_reflns_number_gt                1191
_reflns_number_total             1275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201093u_si_001.cif
_cod_data_source_block           xsc08023
_cod_database_code               4026749